JP2010532312A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2010532312A5 JP2010532312A5 JP2009548293A JP2009548293A JP2010532312A5 JP 2010532312 A5 JP2010532312 A5 JP 2010532312A5 JP 2009548293 A JP2009548293 A JP 2009548293A JP 2009548293 A JP2009548293 A JP 2009548293A JP 2010532312 A5 JP2010532312 A5 JP 2010532312A5
- Authority
- JP
- Japan
- Prior art keywords
- group
- pyrazolo
- pyrimidin
- phenyl
- ylamino
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- -1 guanidinyl group Chemical group 0.000 claims description 448
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 111
- 150000001875 compounds Chemical class 0.000 claims description 84
- 125000000217 alkyl group Chemical group 0.000 claims description 56
- 239000001257 hydrogen Substances 0.000 claims description 33
- 229910052739 hydrogen Inorganic materials 0.000 claims description 33
- 125000003118 aryl group Chemical group 0.000 claims description 28
- 125000001424 substituent group Chemical group 0.000 claims description 28
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 26
- 150000002431 hydrogen Chemical class 0.000 claims description 24
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 19
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 16
- 125000001072 heteroaryl group Chemical group 0.000 claims description 16
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 206010028980 Neoplasm Diseases 0.000 claims description 12
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 10
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims description 9
- 201000011510 cancer Diseases 0.000 claims description 8
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 8
- 125000004076 pyridyl group Chemical group 0.000 claims description 7
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 7
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 6
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 6
- 125000005518 carboxamido group Chemical group 0.000 claims description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 6
- BSCCSDNZEIHXOK-UHFFFAOYSA-N phenyl carbamate Chemical compound NC(=O)OC1=CC=CC=C1 BSCCSDNZEIHXOK-UHFFFAOYSA-N 0.000 claims description 6
- OYRRZWATULMEPF-UHFFFAOYSA-N pyrimidin-4-amine Chemical compound NC1=CC=NC=N1 OYRRZWATULMEPF-UHFFFAOYSA-N 0.000 claims description 6
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 6
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
- 102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 claims description 5
- NTNDIJQLWSJGSJ-UHFFFAOYSA-N 1-(4-methoxyphenyl)-n-(4-morpholin-4-ylphenyl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=CC(OC)=CC=C1N1C2=NC(NC=3C=CC(=CC=3)N3CCOCC3)=NC=C2C=N1 NTNDIJQLWSJGSJ-UHFFFAOYSA-N 0.000 claims description 4
- SSWQBXSNHDXNJR-UHFFFAOYSA-N 1-(4-methoxyphenyl)-n-[4-(4-methylpiperazin-1-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=CC(OC)=CC=C1N1C2=NC(NC=3C=CC(=CC=3)N3CCN(C)CC3)=NC=C2C=N1 SSWQBXSNHDXNJR-UHFFFAOYSA-N 0.000 claims description 4
- ZUFKTYQSDJJFFZ-UHFFFAOYSA-N 1-[(6-fluoro-4h-1,3-benzodioxin-8-yl)methyl]-n-(4-morpholin-4-ylphenyl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C=12OCOCC2=CC(F)=CC=1CN(C1=N2)N=CC1=CN=C2NC(C=C1)=CC=C1N1CCOCC1 ZUFKTYQSDJJFFZ-UHFFFAOYSA-N 0.000 claims description 4
- LKSCRRBMTYKEAT-UHFFFAOYSA-N 1-cycloheptyl-n-(4-piperazin-1-ylphenyl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1CNCCN1C(C=C1)=CC=C1NC1=NC=C(C=NN2C3CCCCCC3)C2=N1 LKSCRRBMTYKEAT-UHFFFAOYSA-N 0.000 claims description 4
- MSIUDSLIFBLRLA-UHFFFAOYSA-N 1-cycloheptyl-n-[4-(2h-tetrazol-5-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1CCCCCC1N1C2=NC(NC=3C=CC(=CC=3)C=3NN=NN=3)=NC=C2C=N1 MSIUDSLIFBLRLA-UHFFFAOYSA-N 0.000 claims description 4
- BIDHRJUVEKTJKT-UHFFFAOYSA-N 2-methoxy-5-[[1-(3-methoxyphenyl)pyrazolo[3,4-d]pyrimidin-6-yl]amino]phenol Chemical compound COC1=CC=CC(N2C3=NC(NC=4C=C(O)C(OC)=CC=4)=NC=C3C=N2)=C1 BIDHRJUVEKTJKT-UHFFFAOYSA-N 0.000 claims description 4
- 125000006291 3-hydroxybenzyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(=C1[H])C([H])([H])* 0.000 claims description 4
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 4
- JYKBEZSKNYJRGG-UHFFFAOYSA-N 4-[(1-cycloheptylpyrazolo[3,4-d]pyrimidin-6-yl)amino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC1=NC=C(C=NN2C3CCCCCC3)C2=N1 JYKBEZSKNYJRGG-UHFFFAOYSA-N 0.000 claims description 4
- 206010006187 Breast cancer Diseases 0.000 claims description 4
- 208000026310 Breast neoplasm Diseases 0.000 claims description 4
- RUUWHQJRWMWXOZ-UHFFFAOYSA-N COC1=CC=CC(=C1)N2C3=NC(=NC=C3C=N2)C4(CC=C(C=C4)N)N Chemical compound COC1=CC=CC(=C1)N2C3=NC(=NC=C3C=N2)C4(CC=C(C=C4)N)N RUUWHQJRWMWXOZ-UHFFFAOYSA-N 0.000 claims description 4
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 4
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 201000010099 disease Diseases 0.000 claims description 4
- 125000002541 furyl group Chemical group 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000004366 heterocycloalkenyl group Chemical group 0.000 claims description 4
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 4
- 125000002757 morpholinyl group Chemical group 0.000 claims description 4
- DMMWKWROYMBMDS-UHFFFAOYSA-N n-(4-morpholin-4-ylphenyl)-1-(pyridin-2-ylmethyl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound N1=CC2=CN=C(NC=3C=CC(=CC=3)N3CCOCC3)N=C2N1CC1=CC=CC=N1 DMMWKWROYMBMDS-UHFFFAOYSA-N 0.000 claims description 4
- BOVLFNSGFMRUHI-UHFFFAOYSA-N n-[4-[(1-cycloheptylpyrazolo[3,4-d]pyrimidin-6-yl)amino]phenyl]methanesulfonamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1NC1=NC=C(C=NN2C3CCCCCC3)C2=N1 BOVLFNSGFMRUHI-UHFFFAOYSA-N 0.000 claims description 4
- 125000004193 piperazinyl group Chemical group 0.000 claims description 4
- 125000003386 piperidinyl group Chemical group 0.000 claims description 4
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 4
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- LRBWSVUGCRFEBL-UHFFFAOYSA-N 1-(1-benzylpiperidin-4-yl)-n-(4-morpholin-4-ylphenyl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C=1C=CC=CC=1CN(CC1)CCC1N(C1=N2)N=CC1=CN=C2NC(C=C1)=CC=C1N1CCOCC1 LRBWSVUGCRFEBL-UHFFFAOYSA-N 0.000 claims description 3
- XCYBMRJTKDZSBM-UHFFFAOYSA-N 1-(cyclopentylmethyl)-n-(4-piperidin-1-ylphenyl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound N1=CC2=CN=C(NC=3C=CC(=CC=3)N3CCCCC3)N=C2N1CC1CCCC1 XCYBMRJTKDZSBM-UHFFFAOYSA-N 0.000 claims description 3
- NPBPEVPENRPELD-UHFFFAOYSA-N 1-cycloheptyl-n-[4-(4-methylpiperazin-1-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C(C=NN2C3CCCCCC3)C2=N1 NPBPEVPENRPELD-UHFFFAOYSA-N 0.000 claims description 3
- QCQZVTRSTWAIOF-UHFFFAOYSA-N 2-methoxy-5-[[1-(4-methoxyphenyl)pyrazolo[3,4-d]pyrimidin-6-yl]amino]phenol Chemical compound C1=CC(OC)=CC=C1N1C2=NC(NC=3C=C(O)C(OC)=CC=3)=NC=C2C=N1 QCQZVTRSTWAIOF-UHFFFAOYSA-N 0.000 claims description 3
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 3
- SMXRCJBCWRHDJE-UHFFFAOYSA-N 7-deaza-8-aza-2-aminopurine Chemical compound NC1=NC=C2C=NNC2=N1 SMXRCJBCWRHDJE-UHFFFAOYSA-N 0.000 claims description 3
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 3
- MFCAMGOTCXUILT-UHFFFAOYSA-N n-[4-[[1-(4-methoxyphenyl)pyrazolo[3,4-d]pyrimidin-6-yl]amino]phenyl]methanesulfonamide Chemical compound C1=CC(OC)=CC=C1N1C2=NC(NC=3C=CC(NS(C)(=O)=O)=CC=3)=NC=C2C=N1 MFCAMGOTCXUILT-UHFFFAOYSA-N 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- LOGAFLFGWNBIIG-UHFFFAOYSA-N pyridin-3-ylcarbamic acid Chemical compound OC(=O)NC1=CC=CN=C1 LOGAFLFGWNBIIG-UHFFFAOYSA-N 0.000 claims description 3
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 3
- XQEMZJJTVBNDOF-UHFFFAOYSA-N 1-(2-phenylphenyl)-n-[4-(2h-tetrazol-5-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound N=1C=C2C=NN(C=3C(=CC=CC=3)C=3C=CC=CC=3)C2=NC=1NC(C=C1)=CC=C1C1=NN=NN1 XQEMZJJTVBNDOF-UHFFFAOYSA-N 0.000 claims description 2
- LRWSKWAKMANXPV-UHFFFAOYSA-N 1-(3-methoxyphenyl)-n-(2,5,8,11,14-pentaoxabicyclo[13.4.0]nonadeca-1(15),16,18-trien-17-yl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound COC1=CC=CC(N2C3=NC(NC=4C=C5OCCOCCOCCOCCOC5=CC=4)=NC=C3C=N2)=C1 LRWSKWAKMANXPV-UHFFFAOYSA-N 0.000 claims description 2
- JIWHVEKKCGYCKC-UHFFFAOYSA-N 1-(3-methoxyphenyl)-n-(4-morpholin-4-ylphenyl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound COC1=CC=CC(N2C3=NC(NC=4C=CC(=CC=4)N4CCOCC4)=NC=C3C=N2)=C1 JIWHVEKKCGYCKC-UHFFFAOYSA-N 0.000 claims description 2
- GTHKIIRCEUCXJH-UHFFFAOYSA-N 1-(3-methoxyphenyl)-n-(4-piperazin-1-ylphenyl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound COC1=CC=CC(N2C3=NC(NC=4C=CC(=CC=4)N4CCNCC4)=NC=C3C=N2)=C1 GTHKIIRCEUCXJH-UHFFFAOYSA-N 0.000 claims description 2
- MFHNGCQLTIZJLF-UHFFFAOYSA-N 1-(3-methoxyphenyl)-n-[4-(2h-tetrazol-5-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound COC1=CC=CC(N2C3=NC(NC=4C=CC(=CC=4)C=4NN=NN=4)=NC=C3C=N2)=C1 MFHNGCQLTIZJLF-UHFFFAOYSA-N 0.000 claims description 2
- CIOYAVYPXDDWOJ-UHFFFAOYSA-N 1-(3-methoxyphenyl)-n-[4-(4-methylsulfonylpiperazin-1-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound COC1=CC=CC(N2C3=NC(NC=4C=CC(=CC=4)N4CCN(CC4)S(C)(=O)=O)=NC=C3C=N2)=C1 CIOYAVYPXDDWOJ-UHFFFAOYSA-N 0.000 claims description 2
- ZRLRPHMIYBFLMQ-UHFFFAOYSA-N 1-(4-iodophenyl)-n-(4-piperidin-1-ylphenyl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=CC(I)=CC=C1N1C2=NC(NC=3C=CC(=CC=3)N3CCCCC3)=NC=C2C=N1 ZRLRPHMIYBFLMQ-UHFFFAOYSA-N 0.000 claims description 2
- PYKBWGLGDQWXLV-UHFFFAOYSA-N 1-(4-methoxyphenyl)-n-(2,5,8,11,14-pentaoxabicyclo[13.4.0]nonadeca-1(15),16,18-trien-17-yl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=CC(OC)=CC=C1N1C2=NC(NC=3C=C4OCCOCCOCCOCCOC4=CC=3)=NC=C2C=N1 PYKBWGLGDQWXLV-UHFFFAOYSA-N 0.000 claims description 2
- YRVUWBVQVHUVOX-UHFFFAOYSA-N 1-(4-methoxyphenyl)-n-(3,4,5-trimethoxyphenyl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=CC(OC)=CC=C1N1C2=NC(NC=3C=C(OC)C(OC)=C(OC)C=3)=NC=C2C=N1 YRVUWBVQVHUVOX-UHFFFAOYSA-N 0.000 claims description 2
- IKFSCGNSSUVZBN-UHFFFAOYSA-N 1-(4-methoxyphenyl)-n-(4-methylsulfonylphenyl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=CC(OC)=CC=C1N1C2=NC(NC=3C=CC(=CC=3)S(C)(=O)=O)=NC=C2C=N1 IKFSCGNSSUVZBN-UHFFFAOYSA-N 0.000 claims description 2
- IEHNIMGOGYPUFD-UHFFFAOYSA-N 1-(4-methoxyphenyl)-n-(4-piperidin-1-ylphenyl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=CC(OC)=CC=C1N1C2=NC(NC=3C=CC(=CC=3)N3CCCCC3)=NC=C2C=N1 IEHNIMGOGYPUFD-UHFFFAOYSA-N 0.000 claims description 2
- HWFPYNTWTBFJRZ-UHFFFAOYSA-N 1-(4-methoxyphenyl)-n-[3-(4-methylpiperazin-1-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=CC(OC)=CC=C1N1C2=NC(NC=3C=C(C=CC=3)N3CCN(C)CC3)=NC=C2C=N1 HWFPYNTWTBFJRZ-UHFFFAOYSA-N 0.000 claims description 2
- WGHXFMZWZMSQMT-UHFFFAOYSA-N 1-(4-methoxyphenyl)-n-[4-(1,2,4-triazol-1-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=CC(OC)=CC=C1N1C2=NC(NC=3C=CC(=CC=3)N3N=CN=C3)=NC=C2C=N1 WGHXFMZWZMSQMT-UHFFFAOYSA-N 0.000 claims description 2
- NVGFVCHSJMXOJQ-UHFFFAOYSA-N 1-(4-methoxyphenyl)-n-[4-(2h-tetrazol-5-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=CC(OC)=CC=C1N1C2=NC(NC=3C=CC(=CC=3)C=3NN=NN=3)=NC=C2C=N1 NVGFVCHSJMXOJQ-UHFFFAOYSA-N 0.000 claims description 2
- PRQIXWUKPMJIJW-UHFFFAOYSA-N 1-(4-methoxyphenyl)-n-[4-(4-methylsulfonylpiperazin-1-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=CC(OC)=CC=C1N1C2=NC(NC=3C=CC(=CC=3)N3CCN(CC3)S(C)(=O)=O)=NC=C2C=N1 PRQIXWUKPMJIJW-UHFFFAOYSA-N 0.000 claims description 2
- AFVHDTGRLLQRQU-UHFFFAOYSA-N 1-(4-methoxyphenyl)-n-naphthalen-1-ylpyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=CC(OC)=CC=C1N1C2=NC(NC=3C4=CC=CC=C4C=CC=3)=NC=C2C=N1 AFVHDTGRLLQRQU-UHFFFAOYSA-N 0.000 claims description 2
- MMLBTCRYWOMKMZ-UHFFFAOYSA-N 1-(4-methoxyphenyl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=CC(OC)=CC=C1N1C2=NC(N)=NC=C2C=N1 MMLBTCRYWOMKMZ-UHFFFAOYSA-N 0.000 claims description 2
- JERQSOGSLYNKSN-UHFFFAOYSA-N 1-[(3,4-dimethoxyphenyl)methyl]-n-(4-piperazin-1-ylphenyl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=C(OC)C(OC)=CC=C1CN1C2=NC(NC=3C=CC(=CC=3)N3CCNCC3)=NC=C2C=N1 JERQSOGSLYNKSN-UHFFFAOYSA-N 0.000 claims description 2
- UCMHHGHSKZGGKC-UHFFFAOYSA-N 1-[(3-methoxyphenyl)methyl]-n-(4-piperazin-1-ylphenyl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound COC1=CC=CC(CN2C3=NC(NC=4C=CC(=CC=4)N4CCNCC4)=NC=C3C=N2)=C1 UCMHHGHSKZGGKC-UHFFFAOYSA-N 0.000 claims description 2
- ZVPPZUMHXCGRGD-UHFFFAOYSA-N 1-[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]-n-(4-morpholin-4-ylphenyl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound COC1=C(C)C=NC(CN2C3=NC(NC=4C=CC(=CC=4)N4CCOCC4)=NC=C3C=N2)=C1C ZVPPZUMHXCGRGD-UHFFFAOYSA-N 0.000 claims description 2
- RWLCTZUSLUIIRR-UHFFFAOYSA-N 1-[3-[[1-(4-methoxyphenyl)pyrazolo[3,4-d]pyrimidin-6-yl]amino]phenyl]ethanol Chemical compound C1=CC(OC)=CC=C1N1C2=NC(NC=3C=C(C=CC=3)C(C)O)=NC=C2C=N1 RWLCTZUSLUIIRR-UHFFFAOYSA-N 0.000 claims description 2
- MWBDIIOUUDTETI-UHFFFAOYSA-N 1-benzyl-n-(4-piperidin-1-ylphenyl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound N1=CC2=CN=C(NC=3C=CC(=CC=3)N3CCCCC3)N=C2N1CC1=CC=CC=C1 MWBDIIOUUDTETI-UHFFFAOYSA-N 0.000 claims description 2
- HTJZFHBHAKJNOX-UHFFFAOYSA-N 1-butyl-n-(4-piperidin-1-ylphenyl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound N1=C2N(CCCC)N=CC2=CN=C1NC(C=C1)=CC=C1N1CCCCC1 HTJZFHBHAKJNOX-UHFFFAOYSA-N 0.000 claims description 2
- JZWWOVYCDFKCTQ-UHFFFAOYSA-N 1-cycloheptyl-n-(4-morpholin-4-ylphenyl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1COCCN1C(C=C1)=CC=C1NC1=NC=C(C=NN2C3CCCCCC3)C2=N1 JZWWOVYCDFKCTQ-UHFFFAOYSA-N 0.000 claims description 2
- OHAYHVBBKFKPGX-UHFFFAOYSA-N 1-cycloheptyl-n-(4-piperidin-1-ylphenyl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1CCCCN1C(C=C1)=CC=C1NC1=NC=C(C=NN2C3CCCCCC3)C2=N1 OHAYHVBBKFKPGX-UHFFFAOYSA-N 0.000 claims description 2
- LJFXJAGGDZXRQX-UHFFFAOYSA-N 1-cycloheptyl-n-(4-pyrazol-1-ylphenyl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1CCCCCC1N1C2=NC(NC=3C=CC(=CC=3)N3N=CC=C3)=NC=C2C=N1 LJFXJAGGDZXRQX-UHFFFAOYSA-N 0.000 claims description 2
- UCEFGXSILYUJIE-UHFFFAOYSA-N 1-cycloheptyl-n-[4-(1-methyltetrazol-5-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound CN1N=NN=C1C(C=C1)=CC=C1NC1=NC=C(C=NN2C3CCCCCC3)C2=N1 UCEFGXSILYUJIE-UHFFFAOYSA-N 0.000 claims description 2
- IPBRJZXTSCTAAI-UHFFFAOYSA-N 1-cycloheptyl-n-[4-(2-morpholin-4-ylethoxy)phenyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C=1C=C(NC=2N=C3N(C4CCCCCC4)N=CC3=CN=2)C=CC=1OCCN1CCOCC1 IPBRJZXTSCTAAI-UHFFFAOYSA-N 0.000 claims description 2
- VQQWSSDIJAORSU-UHFFFAOYSA-N 1-cycloheptyl-n-[4-(4-methylsulfonylpiperazin-1-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1CN(S(=O)(=O)C)CCN1C(C=C1)=CC=C1NC1=NC=C(C=NN2C3CCCCCC3)C2=N1 VQQWSSDIJAORSU-UHFFFAOYSA-N 0.000 claims description 2
- UUQKTIWWHSBBGI-UHFFFAOYSA-N 1-cycloheptyl-n-[4-[(4-methylpiperazin-1-yl)methyl]phenyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1CN(C)CCN1CC(C=C1)=CC=C1NC1=NC=C(C=NN2C3CCCCCC3)C2=N1 UUQKTIWWHSBBGI-UHFFFAOYSA-N 0.000 claims description 2
- ZKWBELIXZBEOLR-UHFFFAOYSA-N 1-methyl-n-(4-piperidin-1-ylphenyl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound N1=C2N(C)N=CC2=CN=C1NC(C=C1)=CC=C1N1CCCCC1 ZKWBELIXZBEOLR-UHFFFAOYSA-N 0.000 claims description 2
- CVYJQYKYFZIBCG-UHFFFAOYSA-N 2-[4-[(1-cycloheptylpyrazolo[3,4-d]pyrimidin-6-yl)amino]phenyl]-2-methyl-1-(4-methylpiperazin-1-yl)propan-1-one Chemical compound C1CN(C)CCN1C(=O)C(C)(C)C(C=C1)=CC=C1NC1=NC=C(C=NN2C3CCCCCC3)C2=N1 CVYJQYKYFZIBCG-UHFFFAOYSA-N 0.000 claims description 2
- GNOXGRKHNMFNLZ-UHFFFAOYSA-N 2-[4-[(1-cycloheptylpyrazolo[3,4-d]pyrimidin-6-yl)amino]phenyl]-2-methylpropanoic acid Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1NC1=NC=C(C=NN2C3CCCCCC3)C2=N1 GNOXGRKHNMFNLZ-UHFFFAOYSA-N 0.000 claims description 2
- NROOCSOXUCZDGS-UHFFFAOYSA-N 2-[4-[(1-cycloheptylpyrazolo[3,4-d]pyrimidin-6-yl)amino]phenyl]-n-propan-2-ylacetamide Chemical compound C1=CC(CC(=O)NC(C)C)=CC=C1NC1=NC=C(C=NN2C3CCCCCC3)C2=N1 NROOCSOXUCZDGS-UHFFFAOYSA-N 0.000 claims description 2
- AMSCDMMOZIJNEF-UHFFFAOYSA-N 2-[4-[(1-cycloheptylpyrazolo[3,4-d]pyrimidin-6-yl)amino]phenyl]ethanol Chemical compound C1=CC(CCO)=CC=C1NC1=NC=C(C=NN2C3CCCCCC3)C2=N1 AMSCDMMOZIJNEF-UHFFFAOYSA-N 0.000 claims description 2
- YFWUKRYNTIIIAA-UHFFFAOYSA-N 2-ethoxy-5-[[1-(4-methoxyphenyl)pyrazolo[3,4-d]pyrimidin-6-yl]amino]phenol Chemical compound C1=C(O)C(OCC)=CC=C1NC1=NC=C(C=NN2C=3C=CC(OC)=CC=3)C2=N1 YFWUKRYNTIIIAA-UHFFFAOYSA-N 0.000 claims description 2
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- GLNFNQVQAATIJH-UHFFFAOYSA-N 2-methoxy-5-[[1-(2-phenylphenyl)pyrazolo[3,4-d]pyrimidin-6-yl]amino]phenol Chemical compound C1=C(O)C(OC)=CC=C1NC1=NC=C(C=NN2C=3C(=CC=CC=3)C=3C=CC=CC=3)C2=N1 GLNFNQVQAATIJH-UHFFFAOYSA-N 0.000 claims description 2
- NHRIKAFOXFZKQA-UHFFFAOYSA-N 3-[6-(4-aminoanilino)pyrazolo[3,4-d]pyrimidin-1-yl]phenol Chemical compound C1=CC(N)=CC=C1NC1=NC=C(C=NN2C=3C=C(O)C=CC=3)C2=N1 NHRIKAFOXFZKQA-UHFFFAOYSA-N 0.000 claims description 2
- SOIGDEMQRVPBLK-UHFFFAOYSA-N 3-[[1-(4-methoxyphenyl)pyrazolo[3,4-d]pyrimidin-6-yl]amino]phenol Chemical compound C1=CC(OC)=CC=C1N1C2=NC(NC=3C=C(O)C=CC=3)=NC=C2C=N1 SOIGDEMQRVPBLK-UHFFFAOYSA-N 0.000 claims description 2
- GTKQJYUCWRMVEV-UHFFFAOYSA-N 4-[4-[6-(3,4-dimethoxyanilino)pyrazolo[3,4-d]pyrimidin-1-yl]phenyl]but-3-yn-1-ol Chemical compound C1=C(OC)C(OC)=CC=C1NC1=NC=C(C=NN2C=3C=CC(=CC=3)C#CCCO)C2=N1 GTKQJYUCWRMVEV-UHFFFAOYSA-N 0.000 claims description 2
- UUTJIZAMHZENAQ-UHFFFAOYSA-N 4-[4-[6-(4-aminoanilino)pyrazolo[3,4-d]pyrimidin-1-yl]phenyl]but-3-yn-1-ol Chemical compound C1=CC(N)=CC=C1NC1=NC=C(C=NN2C=3C=CC(=CC=3)C#CCCO)C2=N1 UUTJIZAMHZENAQ-UHFFFAOYSA-N 0.000 claims description 2
- IPPJIWCVXZIHDK-UHFFFAOYSA-N 4-[6-(4-morpholin-4-ylanilino)pyrazolo[3,4-d]pyrimidin-1-yl]phenol Chemical compound C1=CC(O)=CC=C1N1C2=NC(NC=3C=CC(=CC=3)N3CCOCC3)=NC=C2C=N1 IPPJIWCVXZIHDK-UHFFFAOYSA-N 0.000 claims description 2
- JMKYNBJGIUXATL-UHFFFAOYSA-N 4-[[1-(2-phenylphenyl)pyrazolo[3,4-d]pyrimidin-6-yl]amino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC1=NC=C(C=NN2C=3C(=CC=CC=3)C=3C=CC=CC=3)C2=N1 JMKYNBJGIUXATL-UHFFFAOYSA-N 0.000 claims description 2
- ZAMPQPZOSFLZIW-UHFFFAOYSA-N 4-[[1-(3-methoxyphenyl)pyrazolo[3,4-d]pyrimidin-6-yl]amino]benzoic acid Chemical compound COC1=CC=CC(N2C3=NC(NC=4C=CC(=CC=4)C(O)=O)=NC=C3C=N2)=C1 ZAMPQPZOSFLZIW-UHFFFAOYSA-N 0.000 claims description 2
- TZNKPZOESHQVKX-UHFFFAOYSA-N 4-[[1-(4-methoxyphenyl)pyrazolo[3,4-d]pyrimidin-6-yl]amino]-2-methylphenol Chemical compound C1=CC(OC)=CC=C1N1C2=NC(NC=3C=C(C)C(O)=CC=3)=NC=C2C=N1 TZNKPZOESHQVKX-UHFFFAOYSA-N 0.000 claims description 2
- XFKALRRMCCCGFK-UHFFFAOYSA-N 4-[[1-(4-methoxyphenyl)pyrazolo[3,4-d]pyrimidin-6-yl]amino]benzoic acid Chemical compound C1=CC(OC)=CC=C1N1C2=NC(NC=3C=CC(=CC=3)C(O)=O)=NC=C2C=N1 XFKALRRMCCCGFK-UHFFFAOYSA-N 0.000 claims description 2
- IMNSQKHQDGNNLX-UHFFFAOYSA-N 4-[[1-(4-methoxyphenyl)pyrazolo[3,4-d]pyrimidin-6-yl]amino]phenol Chemical compound C1=CC(OC)=CC=C1N1C2=NC(NC=3C=CC(O)=CC=3)=NC=C2C=N1 IMNSQKHQDGNNLX-UHFFFAOYSA-N 0.000 claims description 2
- 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 claims description 2
- CAOCEOAUKSPUPN-UHFFFAOYSA-N 4-ethylpiperazine-1-carbaldehyde Chemical compound CCN1CCN(C=O)CC1 CAOCEOAUKSPUPN-UHFFFAOYSA-N 0.000 claims description 2
- 125000003143 4-hydroxybenzyl group Chemical group [H]C([*])([H])C1=C([H])C([H])=C(O[H])C([H])=C1[H] 0.000 claims description 2
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000006306 4-iodophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1I 0.000 claims description 2
- 125000004861 4-isopropyl phenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- WMQFRHKLXUDUGC-UHFFFAOYSA-N 5-[(1-cycloheptylpyrazolo[3,4-d]pyrimidin-6-yl)amino]-2-methoxyphenol Chemical compound C1=C(O)C(OC)=CC=C1NC1=NC=C(C=NN2C3CCCCCC3)C2=N1 WMQFRHKLXUDUGC-UHFFFAOYSA-N 0.000 claims description 2
- OBXLLSUUUPFEJN-UHFFFAOYSA-N 5-[[1-(3-hydroxyphenyl)pyrazolo[3,4-d]pyrimidin-6-yl]amino]-2-methoxyphenol Chemical compound C1=C(O)C(OC)=CC=C1NC1=NC=C(C=NN2C=3C=C(O)C=CC=3)C2=N1 OBXLLSUUUPFEJN-UHFFFAOYSA-N 0.000 claims description 2
- JJIHWSUUDQCEGB-UHFFFAOYSA-N 5-[[1-(4-hydroxyphenyl)pyrazolo[3,4-d]pyrimidin-6-yl]amino]-2-methoxyphenol Chemical compound C1=C(O)C(OC)=CC=C1NC1=NC=C(C=NN2C=3C=CC(O)=CC=3)C2=N1 JJIHWSUUDQCEGB-UHFFFAOYSA-N 0.000 claims description 2
- YCVFIKVKPPNWMD-UHFFFAOYSA-N 5-[[1-(4-iodophenyl)pyrazolo[3,4-d]pyrimidin-6-yl]amino]-2-methoxyphenol Chemical compound C1=C(O)C(OC)=CC=C1NC1=NC=C(C=NN2C=3C=CC(I)=CC=3)C2=N1 YCVFIKVKPPNWMD-UHFFFAOYSA-N 0.000 claims description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 2
- 102000003989 Aurora kinases Human genes 0.000 claims description 2
- 108090000433 Aurora kinases Proteins 0.000 claims description 2
- 206010005949 Bone cancer Diseases 0.000 claims description 2
- 208000018084 Bone neoplasm Diseases 0.000 claims description 2
- 208000003174 Brain Neoplasms Diseases 0.000 claims description 2
- QVPBQCLIHFTOIZ-UHFFFAOYSA-N C1CN(CCN1)C2=CC=C(C=C2)NC3=NN(C4=NC=NC=C34)C5=CC=CC=C5C6=CC=CC=C6 Chemical compound C1CN(CCN1)C2=CC=C(C=C2)NC3=NN(C4=NC=NC=C34)C5=CC=CC=C5C6=CC=CC=C6 QVPBQCLIHFTOIZ-UHFFFAOYSA-N 0.000 claims description 2
- TXNWYFLWPOLOLJ-UHFFFAOYSA-N CS(N(CCN1CCOCC1)C(N=C1)=NC=C1NC1=NC=C(C=NN2OC(NC3=NC=CC=C3)=O)C2=N1)(=O)=O Chemical compound CS(N(CCN1CCOCC1)C(N=C1)=NC=C1NC1=NC=C(C=NN2OC(NC3=NC=CC=C3)=O)C2=N1)(=O)=O TXNWYFLWPOLOLJ-UHFFFAOYSA-N 0.000 claims description 2
- 206010009944 Colon cancer Diseases 0.000 claims description 2
- 208000001333 Colorectal Neoplasms Diseases 0.000 claims description 2
- 208000001976 Endocrine Gland Neoplasms Diseases 0.000 claims description 2
- 206010017993 Gastrointestinal neoplasms Diseases 0.000 claims description 2
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 2
- 206010025323 Lymphomas Diseases 0.000 claims description 2
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 2
- 150000001204 N-oxides Chemical class 0.000 claims description 2
- 102000001253 Protein Kinase Human genes 0.000 claims description 2
- 206010039491 Sarcoma Diseases 0.000 claims description 2
- 208000000453 Skin Neoplasms Diseases 0.000 claims description 2
- 208000021712 Soft tissue sarcoma Diseases 0.000 claims description 2
- 208000008385 Urogenital Neoplasms Diseases 0.000 claims description 2
- CKTDDBSAWWUOFZ-UHFFFAOYSA-N [2-[4-[[1-(4-methoxyphenyl)pyrazolo[3,4-d]pyrimidin-6-yl]amino]anilino]-2-oxoethyl] acetate Chemical compound C(C)(=O)OCC(=O)NC1=CC=C(C=C1)NC1=NC=C2C(=N1)N(N=C2)C1=CC=C(C=C1)OC CKTDDBSAWWUOFZ-UHFFFAOYSA-N 0.000 claims description 2
- CAHBGWMUUOOJGM-UHFFFAOYSA-N [4-[(1-cycloheptylpyrazolo[3,4-d]pyrimidin-6-yl)amino]phenyl]-morpholin-4-ylmethanone Chemical compound C=1C=C(NC=2N=C3N(C4CCCCCC4)N=CC3=CN=2)C=CC=1C(=O)N1CCOCC1 CAHBGWMUUOOJGM-UHFFFAOYSA-N 0.000 claims description 2
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 2
- IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 2
- 125000003368 amide group Chemical group 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 125000006269 biphenyl-2-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C(*)C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 210000004556 brain Anatomy 0.000 claims description 2
- 208000025997 central nervous system neoplasm Diseases 0.000 claims description 2
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 2
- IKOKFZXHPKMJDJ-UHFFFAOYSA-N ethyl 2-[4-[(1-cycloheptylpyrazolo[3,4-d]pyrimidin-6-yl)amino]phenyl]-2-methylpropanoate Chemical compound C1=CC(C(C)(C)C(=O)OCC)=CC=C1NC1=NC=C(C=NN2C3CCCCCC3)C2=N1 IKOKFZXHPKMJDJ-UHFFFAOYSA-N 0.000 claims description 2
- QSFFWWWRDDNJTK-UHFFFAOYSA-N ethyl 2-[4-[[1-(4-methoxyphenyl)pyrazolo[3,4-d]pyrimidin-6-yl]amino]anilino]-2-oxoacetate Chemical compound C1=CC(NC(=O)C(=O)OCC)=CC=C1NC1=NC=C(C=NN2C=3C=CC(OC)=CC=3)C2=N1 QSFFWWWRDDNJTK-UHFFFAOYSA-N 0.000 claims description 2
- 201000010536 head and neck cancer Diseases 0.000 claims description 2
- 208000014829 head and neck neoplasm Diseases 0.000 claims description 2
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- 230000002401 inhibitory effect Effects 0.000 claims description 2
- 208000032839 leukemia Diseases 0.000 claims description 2
- 201000005202 lung cancer Diseases 0.000 claims description 2
- 208000020816 lung neoplasm Diseases 0.000 claims description 2
- 208000029559 malignant endocrine neoplasm Diseases 0.000 claims description 2
- 230000001404 mediated effect Effects 0.000 claims description 2
- CTAFNJPQTPFBDJ-UHFFFAOYSA-N n-(1,3-benzodioxol-5-yl)-1-(3-methoxyphenyl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound COC1=CC=CC(N2C3=NC(NC=4C=C5OCOC5=CC=4)=NC=C3C=N2)=C1 CTAFNJPQTPFBDJ-UHFFFAOYSA-N 0.000 claims description 2
- RUEKWHWBQAROJT-UHFFFAOYSA-N n-(2,2-dimethyl-1,3-benzodioxol-5-yl)-1-(4-methoxyphenyl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=CC(OC)=CC=C1N1C2=NC(NC=3C=C4OC(C)(C)OC4=CC=3)=NC=C2C=N1 RUEKWHWBQAROJT-UHFFFAOYSA-N 0.000 claims description 2
- VTCCBKSDGJNVLI-UHFFFAOYSA-N n-(2,3-dihydro-1,4-benzodioxin-6-yl)-1-(4-methoxyphenyl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=CC(OC)=CC=C1N1C2=NC(NC=3C=C4OCCOC4=CC=3)=NC=C2C=N1 VTCCBKSDGJNVLI-UHFFFAOYSA-N 0.000 claims description 2
- OATKTTPFFACPRZ-UHFFFAOYSA-N n-(2,4-dimethoxyphenyl)-1-(3-methoxyphenyl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound COC1=CC=CC(N2C3=NC(NC=4C(=CC(OC)=CC=4)OC)=NC=C3C=N2)=C1 OATKTTPFFACPRZ-UHFFFAOYSA-N 0.000 claims description 2
- UQDVTFIYKOXMHK-UHFFFAOYSA-N n-(3,4-dihydro-2h-1,5-benzodioxepin-7-yl)-1-(4-methoxyphenyl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=CC(OC)=CC=C1N1C2=NC(NC=3C=C4OCCCOC4=CC=3)=NC=C2C=N1 UQDVTFIYKOXMHK-UHFFFAOYSA-N 0.000 claims description 2
- XYMUWFMXHZWFDH-UHFFFAOYSA-N n-(3,4-dimethoxyphenyl)-1-(3-methoxyphenyl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound COC1=CC=CC(N2C3=NC(NC=4C=C(OC)C(OC)=CC=4)=NC=C3C=N2)=C1 XYMUWFMXHZWFDH-UHFFFAOYSA-N 0.000 claims description 2
- BVHBUYVDFKRVFF-UHFFFAOYSA-N n-(3,4-dimethoxyphenyl)-1-(4-iodophenyl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=C(OC)C(OC)=CC=C1NC1=NC=C(C=NN2C=3C=CC(I)=CC=3)C2=N1 BVHBUYVDFKRVFF-UHFFFAOYSA-N 0.000 claims description 2
- NRJALDGHSKBUCL-UHFFFAOYSA-N n-(3-methoxyphenyl)-1-(4-methoxyphenyl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=CC(OC)=CC=C1N1C2=NC(NC=3C=C(OC)C=CC=3)=NC=C2C=N1 NRJALDGHSKBUCL-UHFFFAOYSA-N 0.000 claims description 2
- HROXXJGEUNLQNN-UHFFFAOYSA-N n-(4-morpholin-4-ylphenyl)-1-(1,2,3,4-tetrahydronaphthalen-1-yl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C12=CC=CC=C2CCCC1N(C1=N2)N=CC1=CN=C2NC(C=C1)=CC=C1N1CCOCC1 HROXXJGEUNLQNN-UHFFFAOYSA-N 0.000 claims description 2
- WDOLOEKDCMUNER-UHFFFAOYSA-N n-[3-chloro-4-(methylsulfonylmethyl)phenyl]-1-cycloheptylpyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=C(Cl)C(CS(=O)(=O)C)=CC=C1NC1=NC=C(C=NN2C3CCCCCC3)C2=N1 WDOLOEKDCMUNER-UHFFFAOYSA-N 0.000 claims description 2
- SAUVANXMDWCHCE-UHFFFAOYSA-N n-[4-(4-methylpiperazin-1-yl)phenyl]-1-(2-phenylphenyl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C(C=NN2C=3C(=CC=CC=3)C=3C=CC=CC=3)C2=N1 SAUVANXMDWCHCE-UHFFFAOYSA-N 0.000 claims description 2
- DRDUZQHVFDFHIY-UHFFFAOYSA-N n-[4-[(1-cycloheptylpyrazolo[3,4-d]pyrimidin-6-yl)amino]phenyl]-n-propan-2-ylmethanesulfonamide Chemical compound C1=CC(N(C(C)C)S(C)(=O)=O)=CC=C1NC1=NC=C(C=NN2C3CCCCCC3)C2=N1 DRDUZQHVFDFHIY-UHFFFAOYSA-N 0.000 claims description 2
- SMIKNYWLKWJEOC-UHFFFAOYSA-N n-[4-[(1-phenanthren-4-ylpyrazolo[3,4-d]pyrimidin-6-yl)amino]phenyl]methanesulfonamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1NC1=NC=C(C=NN2C=3C4=C5C=CC=CC5=CC=C4C=CC=3)C2=N1 SMIKNYWLKWJEOC-UHFFFAOYSA-N 0.000 claims description 2
- GHFQOHGVZJRMQN-UHFFFAOYSA-N n-[4-[2-(2-chloroethyl)tetrazol-5-yl]phenyl]-1-cycloheptylpyrazolo[3,4-d]pyrimidin-6-amine Chemical compound ClCCN1N=NC(C=2C=CC(NC=3N=C4N(C5CCCCCC5)N=CC4=CN=3)=CC=2)=N1 GHFQOHGVZJRMQN-UHFFFAOYSA-N 0.000 claims description 2
- PEVOFSWKTNCOEO-UHFFFAOYSA-N n-[4-[[1-(2-phenylphenyl)pyrazolo[3,4-d]pyrimidin-6-yl]amino]phenyl]methanesulfonamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1NC1=NC=C(C=NN2C=3C(=CC=CC=3)C=3C=CC=CC=3)C2=N1 PEVOFSWKTNCOEO-UHFFFAOYSA-N 0.000 claims description 2
- HTQCIAXTJMTNNY-UHFFFAOYSA-N n-[4-[[1-(3-methoxyphenyl)pyrazolo[3,4-d]pyrimidin-6-yl]amino]phenyl]methanesulfonamide Chemical compound COC1=CC=CC(N2C3=NC(NC=4C=CC(NS(C)(=O)=O)=CC=4)=NC=C3C=N2)=C1 HTQCIAXTJMTNNY-UHFFFAOYSA-N 0.000 claims description 2
- IKIGJRNWZVIPEQ-UHFFFAOYSA-N n-[4-[[1-(4-methoxyphenyl)pyrazolo[3,4-d]pyrimidin-6-yl]amino]phenyl]-n-methylmethanesulfonamide Chemical compound C1=CC(OC)=CC=C1N1C2=NC(NC=3C=CC(=CC=3)N(C)S(C)(=O)=O)=NC=C2C=N1 IKIGJRNWZVIPEQ-UHFFFAOYSA-N 0.000 claims description 2
- MPWWQOGTWUNDHR-UHFFFAOYSA-N n-[4-[[1-(4-methoxyphenyl)pyrazolo[3,4-d]pyrimidin-6-yl]amino]phenyl]cyclopropanesulfonamide Chemical compound C1=CC(OC)=CC=C1N1C2=NC(NC=3C=CC(NS(=O)(=O)C4CC4)=CC=3)=NC=C2C=N1 MPWWQOGTWUNDHR-UHFFFAOYSA-N 0.000 claims description 2
- GCCCTCJFSDCQKO-UHFFFAOYSA-N n-[5-[(1-cycloheptylpyrazolo[3,4-d]pyrimidin-6-yl)amino]pyrimidin-2-yl]methanesulfonamide Chemical compound C1=NC(NS(=O)(=O)C)=NC=C1NC1=NC=C(C=NN2C3CCCCCC3)C2=N1 GCCCTCJFSDCQKO-UHFFFAOYSA-N 0.000 claims description 2
- FTKQHVSXQJAEOW-UHFFFAOYSA-N n-[5-[[1-[(3-hydroxyphenyl)methyl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]pyridin-2-yl]methanesulfonamide Chemical compound C1=NC(NS(=O)(=O)C)=CC=C1NC1=NC=C(C=NN2CC=3C=C(O)C=CC=3)C2=N1 FTKQHVSXQJAEOW-UHFFFAOYSA-N 0.000 claims description 2
- 201000008106 ocular cancer Diseases 0.000 claims description 2
- 125000004043 oxo group Chemical group O=* 0.000 claims description 2
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims description 2
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 229940049953 phenylacetate Drugs 0.000 claims description 2
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 2
- 239000000651 prodrug Substances 0.000 claims description 2
- 229940002612 prodrug Drugs 0.000 claims description 2
- 108060006633 protein kinase Proteins 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 201000000849 skin cancer Diseases 0.000 claims description 2
- 239000012453 solvate Substances 0.000 claims description 2
- 125000004001 thioalkyl group Chemical group 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- 230000002485 urinary effect Effects 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 3
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- GLQSIADXDPOALK-KRWDZBQOSA-N n-(4-morpholin-4-ylphenyl)-1-[(1s)-1-phenylethyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1([C@H](C)N2C3=NC(NC=4C=CC(=CC=4)N4CCOCC4)=NC=C3C=N2)=CC=CC=C1 GLQSIADXDPOALK-KRWDZBQOSA-N 0.000 claims 2
- DEVUYWTZRXOMSI-UHFFFAOYSA-N (sulfamoylamino)benzene Chemical compound NS(=O)(=O)NC1=CC=CC=C1 DEVUYWTZRXOMSI-UHFFFAOYSA-N 0.000 claims 1
- SLWXRUGEEGKHRS-UHFFFAOYSA-N 1-(4-methoxy-2-methylphenyl)-n-(4-methylsulfanylphenyl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound CC1=CC(OC)=CC=C1N1C2=NC(NC=3C=CC(SC)=CC=3)=NC=C2C=N1 SLWXRUGEEGKHRS-UHFFFAOYSA-N 0.000 claims 1
- YIWQBKPKRBUMCW-UHFFFAOYSA-N 1-(4-methoxy-2-methylphenyl)-n-[4-(4-methylpiperazin-1-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound CC1=CC(OC)=CC=C1N1C2=NC(NC=3C=CC(=CC=3)N3CCN(C)CC3)=NC=C2C=N1 YIWQBKPKRBUMCW-UHFFFAOYSA-N 0.000 claims 1
- RLLTZIQOXRLOKD-UHFFFAOYSA-N 1-(4-methoxy-2-methylphenyl)-n-[4-(trifluoromethoxy)phenyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound CC1=CC(OC)=CC=C1N1C2=NC(NC=3C=CC(OC(F)(F)F)=CC=3)=NC=C2C=N1 RLLTZIQOXRLOKD-UHFFFAOYSA-N 0.000 claims 1
- CUGFPQWKFARRJQ-UHFFFAOYSA-N 1-(4-methoxyphenyl)-n-(4-methylsulfanylphenyl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=CC(OC)=CC=C1N1C2=NC(NC=3C=CC(SC)=CC=3)=NC=C2C=N1 CUGFPQWKFARRJQ-UHFFFAOYSA-N 0.000 claims 1
- SOMQXJCZKFSGHR-UHFFFAOYSA-N 1-[(4-methoxyphenyl)methyl]-n-(4-piperazin-1-ylphenyl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=CC(OC)=CC=C1CN1C2=NC(NC=3C=CC(=CC=3)N3CCNCC3)=NC=C2C=N1 SOMQXJCZKFSGHR-UHFFFAOYSA-N 0.000 claims 1
- ZLQISKMDKDTLHV-UHFFFAOYSA-N 1-[4-[(1-cycloheptylpyrazolo[3,4-d]pyrimidin-6-yl)amino]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1NC1=NC=C(C=NN2C3CCCCCC3)C2=N1 ZLQISKMDKDTLHV-UHFFFAOYSA-N 0.000 claims 1
- CZQHHUQMWBAGCO-UHFFFAOYSA-N 1-[4-[(1-cycloheptylpyrazolo[3,4-d]pyrimidin-6-yl)amino]phenyl]-3-propylurea Chemical compound C1=CC(NC(=O)NCCC)=CC=C1NC1=NC=C(C=NN2C3CCCCCC3)C2=N1 CZQHHUQMWBAGCO-UHFFFAOYSA-N 0.000 claims 1
- SUHFWBWUWZPUAT-UHFFFAOYSA-N 1-cycloheptyl-n-(4-thiomorpholin-4-ylphenyl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1CSCCN1C(C=C1)=CC=C1NC1=NC=C(C=NN2C3CCCCCC3)C2=N1 SUHFWBWUWZPUAT-UHFFFAOYSA-N 0.000 claims 1
- AOQAAVXIWZSHIB-UHFFFAOYSA-N 1-cycloheptyl-n-[4-(2-methyltetrazol-5-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound CN1N=NC(C=2C=CC(NC=3N=C4N(C5CCCCCC5)N=CC4=CN=3)=CC=2)=N1 AOQAAVXIWZSHIB-UHFFFAOYSA-N 0.000 claims 1
- FOCNLUQWJYCAKS-UHFFFAOYSA-N 1-cycloheptyl-n-[4-(methylsulfonylmethyl)phenyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=CC(CS(=O)(=O)C)=CC=C1NC1=NC=C(C=NN2C3CCCCCC3)C2=N1 FOCNLUQWJYCAKS-UHFFFAOYSA-N 0.000 claims 1
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- CJSBUFUIJSGDQF-UHFFFAOYSA-N 2-[4-[(1-cycloheptylpyrazolo[3,4-d]pyrimidin-6-yl)amino]phenyl]-1-(4-ethylpiperazin-1-yl)ethanone Chemical compound C1CN(CC)CCN1C(=O)CC(C=C1)=CC=C1NC1=NC=C(C=NN2C3CCCCCC3)C2=N1 CJSBUFUIJSGDQF-UHFFFAOYSA-N 0.000 claims 1
- IHLCIFVPIGSHHS-UHFFFAOYSA-N 2-methoxy-4-[[1-(4-methoxyphenyl)pyrazolo[3,4-d]pyrimidin-6-yl]amino]phenol Chemical compound C1=CC(OC)=CC=C1N1C2=NC(NC=3C=C(OC)C(O)=CC=3)=NC=C2C=N1 IHLCIFVPIGSHHS-UHFFFAOYSA-N 0.000 claims 1
- JIZINHLGUOALGX-UHFFFAOYSA-N 2-methoxy-5-[[1-(4-methoxy-2-methylphenyl)pyrazolo[3,4-d]pyrimidin-6-yl]amino]phenol Chemical compound CC1=CC(OC)=CC=C1N1C2=NC(NC=3C=C(O)C(OC)=CC=3)=NC=C2C=N1 JIZINHLGUOALGX-UHFFFAOYSA-N 0.000 claims 1
- LTUNEEBTZOCCDO-UHFFFAOYSA-N 3-[[1-(3-methoxyphenyl)pyrazolo[3,4-d]pyrimidin-6-yl]amino]phenol Chemical compound COC1=CC=CC(N2C3=NC(NC=4C=C(O)C=CC=4)=NC=C3C=N2)=C1 LTUNEEBTZOCCDO-UHFFFAOYSA-N 0.000 claims 1
- NPTJPXPAMQOJML-UHFFFAOYSA-N 4-methoxy-1-n-[1-(4-methoxyphenyl)pyrazolo[3,4-d]pyrimidin-6-yl]benzene-1,3-diamine Chemical compound C1=CC(OC)=CC=C1N1C2=NC(NC=3C=C(N)C(OC)=CC=3)=NC=C2C=N1 NPTJPXPAMQOJML-UHFFFAOYSA-N 0.000 claims 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 1
- 102000016736 Cyclin Human genes 0.000 claims 1
- 108050006400 Cyclin Proteins 0.000 claims 1
- 108091000080 Phosphotransferase Proteins 0.000 claims 1
- 125000005605 benzo group Chemical group 0.000 claims 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 1
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims 1
- 230000001419 dependent effect Effects 0.000 claims 1
- 230000003834 intracellular effect Effects 0.000 claims 1
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 claims 1
- HWPGNNZUONMINL-UHFFFAOYSA-N methyl 3-[4-[[1-(4-methoxyphenyl)pyrazolo[3,4-d]pyrimidin-6-yl]amino]anilino]-3-oxopropanoate Chemical compound C1=CC(NC(=O)CC(=O)OC)=CC=C1NC1=NC=C(C=NN2C=3C=CC(OC)=CC=3)C2=N1 HWPGNNZUONMINL-UHFFFAOYSA-N 0.000 claims 1
- QGGYIEQRZQXKMP-UHFFFAOYSA-N n-(2-morpholin-4-ylethyl)methanesulfonamide Chemical group CS(=O)(=O)NCCN1CCOCC1 QGGYIEQRZQXKMP-UHFFFAOYSA-N 0.000 claims 1
- DCNAEEPZTJYBNZ-UHFFFAOYSA-N n-(4-morpholin-4-ylphenyl)-1h-pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1COCCN1C(C=C1)=CC=C1NC1=NC=C(C=NN2)C2=N1 DCNAEEPZTJYBNZ-UHFFFAOYSA-N 0.000 claims 1
- FGZOFXYEPAPOMM-UHFFFAOYSA-N n-[4-[(1-cycloheptylpyrazolo[3,4-d]pyrimidin-6-yl)amino]phenyl]thiophene-2-sulfonamide Chemical compound C=1C=CSC=1S(=O)(=O)NC(C=C1)=CC=C1NC(N=C12)=NC=C1C=NN2C1CCCCCC1 FGZOFXYEPAPOMM-UHFFFAOYSA-N 0.000 claims 1
- CGEKMFYYLMQCKN-UHFFFAOYSA-N n-[4-[[1-(4-methoxy-2-methylphenyl)pyrazolo[3,4-d]pyrimidin-6-yl]amino]phenyl]methanesulfonamide Chemical compound CC1=CC(OC)=CC=C1N1C2=NC(NC=3C=CC(NS(C)(=O)=O)=CC=3)=NC=C2C=N1 CGEKMFYYLMQCKN-UHFFFAOYSA-N 0.000 claims 1
- MUJPXGWSJHJOJE-UHFFFAOYSA-N n-[4-[[1-(4-methoxyphenyl)pyrazolo[3,4-d]pyrimidin-6-yl]amino]phenyl]acetamide Chemical compound C1=CC(OC)=CC=C1N1C2=NC(NC=3C=CC(NC(C)=O)=CC=3)=NC=C2C=N1 MUJPXGWSJHJOJE-UHFFFAOYSA-N 0.000 claims 1
- XDIIJQFNVMXIJQ-UHFFFAOYSA-N n-methylacetohydrazide Chemical compound CN(N)C(C)=O XDIIJQFNVMXIJQ-UHFFFAOYSA-N 0.000 claims 1
- CMPQUABWPXYYSH-UHFFFAOYSA-N phenyl phosphate Chemical compound OP(O)(=O)OC1=CC=CC=C1 CMPQUABWPXYYSH-UHFFFAOYSA-N 0.000 claims 1
- 102000020233 phosphotransferase Human genes 0.000 claims 1
- HHVIWHSLTBBAGK-UHFFFAOYSA-N piperazin-1-ylphosphonic acid Chemical compound OP(O)(=O)N1CCNCC1 HHVIWHSLTBBAGK-UHFFFAOYSA-N 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
- 208000037964 urogenital cancer Diseases 0.000 claims 1
- ILJNKUSQFWZNCT-UHFFFAOYSA-N 1-(furan-2-ylmethyl)-n-(4-piperazin-1-ylphenyl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound N1=CC2=CN=C(NC=3C=CC(=CC=3)N3CCNCC3)N=C2N1CC1=CC=CO1 ILJNKUSQFWZNCT-UHFFFAOYSA-N 0.000 description 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- ZJIJSTNBCKPMOY-UHFFFAOYSA-N 1-(1h-indol-4-yl)-n-[4-(4-methylpiperazin-1-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C(C=NN2C=3C=4C=CNC=4C=CC=3)C2=N1 ZJIJSTNBCKPMOY-UHFFFAOYSA-N 0.000 description 1
- ZDYSIKQIHZXLNG-UHFFFAOYSA-N 1-(2,3-dihydro-1h-inden-2-yl)-n-(4-morpholin-4-ylphenyl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1C2=CC=CC=C2CC1N(C1=N2)N=CC1=CN=C2NC(C=C1)=CC=C1N1CCOCC1 ZDYSIKQIHZXLNG-UHFFFAOYSA-N 0.000 description 1
- ZMINETKADICQPZ-UHFFFAOYSA-N 1-(3-methoxyphenyl)-n-[4-(4-methylpiperazin-1-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound COC1=CC=CC(N2C3=NC(NC=4C=CC(=CC=4)N4CCN(C)CC4)=NC=C3C=N2)=C1 ZMINETKADICQPZ-UHFFFAOYSA-N 0.000 description 1
- CZYXHXGZCOOFJN-UHFFFAOYSA-N 1-(4-methoxy-2-methylphenyl)-n-(4-methoxyphenyl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=CC(OC)=CC=C1NC1=NC=C(C=NN2C=3C(=CC(OC)=CC=3)C)C2=N1 CZYXHXGZCOOFJN-UHFFFAOYSA-N 0.000 description 1
- NYVOBTUFNXUIBR-UHFFFAOYSA-N 1-(7-methyl-1h-indol-4-yl)-n-[4-(4-methylpiperazin-1-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C(C=NN2C=3C=4C=CNC=4C(C)=CC=3)C2=N1 NYVOBTUFNXUIBR-UHFFFAOYSA-N 0.000 description 1
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
- HWRHBUPIPIHFPC-FQEVSTJZSA-N 1-[(1s)-2,3-dihydro-1h-inden-1-yl]-n-[2-(4-nitrophenyl)ethyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=CC([N+](=O)[O-])=CC=C1CCNC1=NC=C(C=NN2[C@@H]3C4=CC=CC=C4CC3)C2=N1 HWRHBUPIPIHFPC-FQEVSTJZSA-N 0.000 description 1
- IQAZMZNTCHBNLU-SFHVURJKSA-N 1-[(1s)-2,3-dihydro-1h-inden-1-yl]-n-[4-(2h-tetrazol-5-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound N1=C2N([C@@H]3C4=CC=CC=C4CC3)N=CC2=CN=C1NC(C=C1)=CC=C1C1=NN=NN1 IQAZMZNTCHBNLU-SFHVURJKSA-N 0.000 description 1
- OYFXQQXMGDPNIR-UHFFFAOYSA-N 1-[6-(4-aminoanilino)pyrazolo[3,4-d]pyrimidin-1-yl]-2,3-dihydro-1h-inden-4-ol Chemical compound C1=CC(N)=CC=C1NC1=NC=C(C=NN2C3C4=C(C(=CC=C4)O)CC3)C2=N1 OYFXQQXMGDPNIR-UHFFFAOYSA-N 0.000 description 1
- GSFBKTFJGAQAHB-UHFFFAOYSA-N 1-cycloheptyl-n-[4-(2-ethenyltetrazol-5-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C=CN1N=NC(C=2C=CC(NC=3N=C4N(C5CCCCCC5)N=CC4=CN=3)=CC=2)=N1 GSFBKTFJGAQAHB-UHFFFAOYSA-N 0.000 description 1
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 description 1
- KIPQPQGBKAPXGZ-UHFFFAOYSA-N 2-[4-[(1-cycloheptylpyrazolo[3,4-d]pyrimidin-6-yl)amino]phenyl]-n-methylacetamide Chemical compound C1=CC(CC(=O)NC)=CC=C1NC1=NC=C(C=NN2C3CCCCCC3)C2=N1 KIPQPQGBKAPXGZ-UHFFFAOYSA-N 0.000 description 1
- TYFBSIQEIUWHAG-UHFFFAOYSA-N 2-[4-[(1-cycloheptylpyrazolo[3,4-d]pyrimidin-6-yl)amino]phenyl]acetic acid Chemical compound C1=CC(CC(=O)O)=CC=C1NC1=NC=C(C=NN2C3CCCCCC3)C2=N1 TYFBSIQEIUWHAG-UHFFFAOYSA-N 0.000 description 1
- ZDBMVTIWOSBGMD-UHFFFAOYSA-N 2-[4-[4-[(1-cycloheptylpyrazolo[3,4-d]pyrimidin-6-yl)amino]phenyl]piperazin-1-yl]ethanol Chemical compound C1CN(CCO)CCN1C(C=C1)=CC=C1NC1=NC=C(C=NN2C3CCCCCC3)C2=N1 ZDBMVTIWOSBGMD-UHFFFAOYSA-N 0.000 description 1
- DINXLRXOTQBCNI-UHFFFAOYSA-N 2-[4-[[1-(4-methoxyphenyl)pyrazolo[3,4-d]pyrimidin-6-yl]amino]phenyl]ethanol Chemical compound C1=CC(OC)=CC=C1N1C2=NC(NC=3C=CC(CCO)=CC=3)=NC=C2C=N1 DINXLRXOTQBCNI-UHFFFAOYSA-N 0.000 description 1
- IOAMCESAONAQEV-UHFFFAOYSA-N 2-methoxy-4-[[1-(3-methoxyphenyl)pyrazolo[3,4-d]pyrimidin-6-yl]amino]phenol Chemical compound COC1=CC=CC(N2C3=NC(NC=4C=C(OC)C(O)=CC=4)=NC=C3C=N2)=C1 IOAMCESAONAQEV-UHFFFAOYSA-N 0.000 description 1
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical group NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 description 1
- JLAKCHGEEBPDQI-UHFFFAOYSA-N 4-(4-fluorobenzyl)piperidine Chemical compound C1=CC(F)=CC=C1CC1CCNCC1 JLAKCHGEEBPDQI-UHFFFAOYSA-N 0.000 description 1
- BGNGWHSBYQYVRX-UHFFFAOYSA-N 4-(dimethylamino)benzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C=C1 BGNGWHSBYQYVRX-UHFFFAOYSA-N 0.000 description 1
- QLGVACCKJRKICA-UHFFFAOYSA-N 4-[(1-cycloheptylpyrazolo[3,4-d]pyrimidin-6-yl)amino]benzonitrile Chemical compound C1=CC(C#N)=CC=C1NC1=NC=C(C=NN2C3CCCCCC3)C2=N1 QLGVACCKJRKICA-UHFFFAOYSA-N 0.000 description 1
- GVOXMLRIPSSWTB-UHFFFAOYSA-N 4-[6-(4-aminoanilino)pyrazolo[3,4-d]pyrimidin-1-yl]phenol Chemical compound C1=CC(N)=CC=C1NC1=NC=C(C=NN2C=3C=CC(O)=CC=3)C2=N1 GVOXMLRIPSSWTB-UHFFFAOYSA-N 0.000 description 1
- MKVMQIFACXQHDI-SFHVURJKSA-N 4-[[1-[(1s)-2,3-dihydro-1h-inden-1-yl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]-n'-hydroxybenzenecarboximidamide Chemical compound C1=CC(C(=N/O)/N)=CC=C1NC1=NC=C(C=NN2[C@@H]3C4=CC=CC=C4CC3)C2=N1 MKVMQIFACXQHDI-SFHVURJKSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- SVNGUXYXAAIQLJ-UHFFFAOYSA-N C1CC2=C(C=CC=C2C1N3C4=NC(=NC=C4C=N3)NC5=CC=C(C=C5)N)C6=CC=CC=C6C(=O)O Chemical compound C1CC2=C(C=CC=C2C1N3C4=NC(=NC=C4C=N3)NC5=CC=C(C=C5)N)C6=CC=CC=C6C(=O)O SVNGUXYXAAIQLJ-UHFFFAOYSA-N 0.000 description 1
- FFSNZQAMGPMHQO-UHFFFAOYSA-N CN1CCN(CC1)C2=CC=C(C=C2)NC3=NC=C4C=NN(C4=N3)C5CCC6=C(C=CC=C56)C7=CC=CC=C7C(=O)O Chemical compound CN1CCN(CC1)C2=CC=C(C=C2)NC3=NC=C4C=NN(C4=N3)C5CCC6=C(C=CC=C56)C7=CC=CC=C7C(=O)O FFSNZQAMGPMHQO-UHFFFAOYSA-N 0.000 description 1
- PHASHKHNXXSYJE-UHFFFAOYSA-N CS(=O)(=O)N(C1=CC=C(C=C1)NC2=NC=C3C=NN(C3=N2)C4CCC5=C(C=CC=C45)C6=CC=CC=C6C(=O)O)S(=O)(=O)C Chemical compound CS(=O)(=O)N(C1=CC=C(C=C1)NC2=NC=C3C=NN(C3=N2)C4CCC5=C(C=CC=C45)C6=CC=CC=C6C(=O)O)S(=O)(=O)C PHASHKHNXXSYJE-UHFFFAOYSA-N 0.000 description 1
- 102000003903 Cyclin-dependent kinases Human genes 0.000 description 1
- 108090000266 Cyclin-dependent kinases Proteins 0.000 description 1
- 241001024304 Mino Species 0.000 description 1
- GMZVRMREEHBGGF-UHFFFAOYSA-N Piracetam Chemical compound NC(=O)CN1CCCC1=O GMZVRMREEHBGGF-UHFFFAOYSA-N 0.000 description 1
- YAUNIGRRZBDFJH-UHFFFAOYSA-N [1-[6-[4-[bis(methylsulfonyl)amino]anilino]pyrazolo[3,4-d]pyrimidin-1-yl]-2,3-dihydro-1H-inden-4-yl] ditert-butyl phosphate Chemical compound CC(C)(C)OP(=O)(Oc1cccc2C(CCc12)n1ncc2cnc(Nc3ccc(cc3)N(S(C)(=O)=O)S(C)(=O)=O)nc12)OC(C)(C)C YAUNIGRRZBDFJH-UHFFFAOYSA-N 0.000 description 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 1
- 208000024519 eye neoplasm Diseases 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 230000011278 mitosis Effects 0.000 description 1
- GJKRIXGECJEURU-UHFFFAOYSA-N n-(1,3-benzodioxol-5-yl)-1-cycloheptylpyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=C2OCOC2=CC=C1NC(N=C12)=NC=C1C=NN2C1CCCCCC1 GJKRIXGECJEURU-UHFFFAOYSA-N 0.000 description 1
- QBMAGORLPVPXCO-UHFFFAOYSA-N n-(3,4-dimethoxyphenyl)-1-(4-methoxyphenyl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=CC(OC)=CC=C1N1C2=NC(NC=3C=C(OC)C(OC)=CC=3)=NC=C2C=N1 QBMAGORLPVPXCO-UHFFFAOYSA-N 0.000 description 1
- ICSYRROXXVMJEA-UHFFFAOYSA-N n-(4-morpholin-4-ylphenyl)-1-(2-phenylphenyl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1COCCN1C(C=C1)=CC=C1NC1=NC=C(C=NN2C=3C(=CC=CC=3)C=3C=CC=CC=3)C2=N1 ICSYRROXXVMJEA-UHFFFAOYSA-N 0.000 description 1
- FTXZNUXMOADWHI-UHFFFAOYSA-N n-(4-morpholin-4-ylphenyl)-1-(naphthalen-1-ylmethyl)pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C=1C=CC2=CC=CC=C2C=1CN(C1=N2)N=CC1=CN=C2NC(C=C1)=CC=C1N1CCOCC1 FTXZNUXMOADWHI-UHFFFAOYSA-N 0.000 description 1
- RCMJHHVMQLVCIW-UHFFFAOYSA-N n-(4-piperidin-1-ylphenyl)-1-propan-2-ylpyrazolo[3,4-d]pyrimidin-6-amine Chemical compound N1=C2N(C(C)C)N=CC2=CN=C1NC(C=C1)=CC=C1N1CCCCC1 RCMJHHVMQLVCIW-UHFFFAOYSA-N 0.000 description 1
- NDFDIONLUXHRRA-UHFFFAOYSA-N n-[1-[6-[4-[bis(methylsulfonyl)amino]anilino]pyrazolo[3,4-d]pyrimidin-1-yl]-2,3-dihydro-1h-inden-5-yl]acetamide Chemical compound C1CC2=CC(NC(=O)C)=CC=C2C1N(C1=N2)N=CC1=CN=C2NC1=CC=C(N(S(C)(=O)=O)S(C)(=O)=O)C=C1 NDFDIONLUXHRRA-UHFFFAOYSA-N 0.000 description 1
- VQLBPSKCCYEXFF-FQEVSTJZSA-N n-[2-(4-aminophenyl)ethyl]-1-[(1s)-2,3-dihydro-1h-inden-1-yl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound C1=CC(N)=CC=C1CCNC1=NC=C(C=NN2[C@@H]3C4=CC=CC=C4CC3)C2=N1 VQLBPSKCCYEXFF-FQEVSTJZSA-N 0.000 description 1
- RPQLNPIJBWIIHD-UHFFFAOYSA-N n-[4-[(1-cycloheptylpyrazolo[3,4-d]pyrimidin-6-yl)amino]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1NC1=NC=C(C=NN2C3CCCCCC3)C2=N1 RPQLNPIJBWIIHD-UHFFFAOYSA-N 0.000 description 1
- ZDAPKQDOWXAPLV-UHFFFAOYSA-N n-[4-[[1-(4-hydroxy-2,3-dihydro-1h-inden-1-yl)pyrazolo[3,4-d]pyrimidin-6-yl]amino]phenyl]methanesulfonamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1NC1=NC=C(C=NN2C3C4=C(C(=CC=C4)O)CC3)C2=N1 ZDAPKQDOWXAPLV-UHFFFAOYSA-N 0.000 description 1
- PARUULGUCQEWNM-UHFFFAOYSA-N n-[5-[(1-cycloheptylpyrazolo[3,4-d]pyrimidin-6-yl)amino]pyridin-2-yl]methanesulfonamide Chemical compound C1=NC(NS(=O)(=O)C)=CC=C1NC1=NC=C(C=NN2C3CCCCCC3)C2=N1 PARUULGUCQEWNM-UHFFFAOYSA-N 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000006633 tert-butoxycarbonylamino group Chemical group 0.000 description 1
- LMQGGWATBUQBNT-UHFFFAOYSA-N tert-butyl 7-methyl-4-[6-[4-(4-methylpiperazin-1-yl)anilino]pyrazolo[3,4-d]pyrimidin-1-yl]indole-1-carboxylate Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C(C=NN2C=3C=4C=CN(C=4C(C)=CC=3)C(=O)OC(C)(C)C)C2=N1 LMQGGWATBUQBNT-UHFFFAOYSA-N 0.000 description 1
Description
本発明は、例えば以下の項目を提供する。
(項目1)
式(I)の化合物、そのプロドラッグ、多形体、互変異性体、エナンチオマー、立体異性体、溶媒和化合物、N−オキシド誘導体又は薬理学的に許容できる塩。
(式中、R 1 は水素又はハロ基であり、
R 2 は−L 1 −R a であり、
L 1 は結合又はアルキル基であり、
R a はシクロヘキシル基、シクロヘプチル基、ピペリジニル基、ピロリジニル基、フリル基、チエニル基、モルホリニル基、ピリジニル基又はピリミジニル基であり、各々1〜3個の置換基で任意に置換されてもよいか、又は、
R a は置換フェニル基であり、
R 3 は−R b −L 2 −R c であり、
R b はアリール基、ヘテロアリール基、シクロアルキル基又はヘテロシクロアルキル基であって、1〜3個の置換基で任意に置換されてもよく、前記置換基のうちの2つが隣接するときは、それらが結合する1つ以上の原子と共に、0〜6個のヘテロ環原子を有する5〜16員環を形成し、
L 2 は結合、−(CR x R y ) n −、−N=、−O−、−S−、−SO−、−SO 2 −、−CO−、−CO−O−、−O−CO−、−NR x −、−NR x −CO−、−NR x −SO 2 −、−CO−NR x −、−SO 2 −NR x −、−NR x −CO−O−、−NR x −SO 2 −O−、−NR x −CO−NR y −、−NR x −SO 2 −NR y −、−CO−NR x −NR y −、−SO 2 −NR x −NR y −、−NR x −CO−CO−O−、−NR x −SO 2 −SO 2 −O−、−S(O) 2 −N x −CO−R y −、−CO−N x −S(O) 2 −R y −又は−(NR x R y )C=N−O−であり、
R c は水素、アルキル基、アルケニル基、アルキニル基、グアニジニル基、シクロアルキル基、ヘテロシクロアルキル基、シクロアルケニル基、ヘテロシクロアルケニル基、アリール基、ヘテロアリール基、(シクロアルキル)アルキル基、(ヘテロシクロアルキル)アルキル基、(シクロアルケニル)アルキル基、(ヘテロシクロアルケニル)アルキル基、アラルキル基又はヘテロアラルキル基であって、かつ、水素を除いて、1〜3個の置換基で任意に置換されてもよく、
R x 及びR y は各々独立に、水素、ヒドロキシ基、アルキル基、アルコキシ基、アミノ基、−CO−アルキル基、−CO−アリール基、−SO 2 −アルキル基、−SO 2 −アリール基、−SO 2 −ヘテロアリール基又は−P(O)(O−アルキル) 2 であり、
R x 又はR y のアルキル部分又はアリール部分は、1〜3個の置換基で任意に置換されてもよく、
nは0、1、2、又は3である)
(項目2)
R a 、R b 、R c 、R x 及びR y 上の前記1〜3個の任意の置換基が、各々独立に、アルキル基、アルケニル基、アルキニル基、シクロアルキル基、ヘテロシクロアルキル基、アリール基、ヘテロアリール基、アリールアルキル基、ヘテロアリールアルキル基、−OR、−SR、−NRR’、オキソ基、−C(O)−OR、−C(O)−NRR’、ハロ基、CN,NO 2 ,N 3 ,−C(O)R”,−P(O)(OR)(OR’),−O−P(O)(OR)(OR’),−NR−P(O)(OR)(OR’),−S(O) 2 −OR、−O−S(O) 2 −OR、−NR−S(O) 2 −OR’,−NR−C(O)−OR”,−NR−C(O)−NRR’、−NR−C(S)−NRR’、−C(S)−NRR’及びチオアルキル基であり、
R及びR’が各々独立に、水素、アルキル基、シクロアルキル基、ヘテロシクロアルキル基、アリール基、ヘテロアリール基、アラルキル基又はヘテロアラルキル基であって、
かつ、R”がアルキル基、シクロアルキル基、ヘテロシクロアルキル基、アリール基、ヘテロアリール基、アラルキル基又はヘテロアラルキル基である、項目1記載の化合物。
(項目3)
R 1 が水素である、項目1記載の化合物。
(項目4)
L 1 が結合である、項目1記載の化合物。
(項目5)
R a がシクロヘプチル基である、項目4記載の化合物。
(項目6)
R a が1〜3個の置換基により置換されたフェニル基である、項目4記載の化合物。
(項目7)
R a がパラ位に少なくとも1個の置換基を有するフェニル基である、項目6記載の化合物。
(項目8)
R 2 が1−(ビフェニル−2−イル)基、4−ヒドロキシフェニル基、4−(ヒドロキシメチル)フェニル基、3−(ヒドロキシエチル)フェニル基、4−(クロロメチル)フェニル基、4−(tert−ブトキシカルボニル)フェニル基、2−(tert−ブトキシカルボキサミド)フェニル基、4−(tert−ブトキシカルボキサミド)フェニル基、3−メトキシフェニル基、4−メトキシフェニル基、3,4−ジメトキシフェニル基、4−ヨードフェニル基、4−メトキシ−2−メチルフェニル基、4−メトキシ−3−メチルフェニル基、4−アセチルフェニル基、3−アセチルフェニル基、4−(ジエトキシホスホリルオキシ)フェニル基、4−アミノフェニル基、4−ニトロフェニル基、4−アセトアミドフェニル基、3−アセトアミドフェニル基、2−アセトアミドフェニル基、4−(tert−ブトキシカルボキサミド)フェニル基、4−(ジメチルアミノエトキシ)フェニル基、5−メトキシ−2,4−ジニトロフェニル基、3−メトキシ−2,4−ジニトロフェニル基、4−(モルホリン−4−イルカルボニル)フェニル基、4−(ジメチルアミノ)フェニル基、4−メトキシカルボニル−3−フルオロフェニル基、4−(ジ(シクロプロピルカルボニル)アミノ)フェニル基、2−メチルチオフェニル基、2−エチルチオフェニル基、3−(イソプロピルオキシ)フェニル基、4−イソプロピルフェニル基、4−(メトキシアセトアミド)フェニル基、4−(イソプロピルアセトアミド)フェニル基、4−(ジメチルアミノアセトアミド)フェニル基、4−メトキシ−3−(トリフルオロメチル)フェニル基、4−(アクリルアミド)フェニル基、4−(ジ(2−フラニルカルボキシ)アミド)フェニル基、4−(2−フラニル)カルボキサミドフェニル基、4−((エトキシカルボニル)メチルカルボキサミド)フェニル基、4−(シクロプロピルカルボキサミド)フェニル基、4−(トリフルオロメトキシ)フェニル基、4−(2−(ピペリジン−1−イル)アセトアミド)フェニル基、4−((tert−ブトキシカルボキサミド)メチルカルボキシアミド)フェニル基、2−ビニルフェニル基、2−(メチルスルホニル)フェニル基、4−(2−(2−メチル−イミダゾール−1−イル)アセトアミド)フェニル基、4−(2−(イミダゾール−1−イル)アセトアミド)フェニル基、4−(2−(ピロリジン−1−イル)アセトアミド)フェニル基、4−(3−(ピロリジン−1−イル)プロパンアミド)フェニル基、4−(2−(ピロリジン−1−イル)アセトアミド)フェニル基、4−(2−(4−メチルピペラジン−1−イル)アセトアミド)フェニル基、4−(3−(4−メチルピペラジン−1−イル)プロパンアミド)フェニル基、4−(3−(イミダゾール−イル)プロパンアミド)フェニル基、4−((4−メトキシカルボニル)ブタンアミド)フェニル基、4−((2−ビス(2−ヒドロキシエチル)アミノ)アセトアミド)フェニル基、4−(シクロヘキシルカルボキサミド)フェニル基、4−(ビス(シクロヘキシルカルボニル)アミノ)フェニル基、4−((N−モルホリニル)カルボキサミド)フェニル基、4−(2−(ピリジン−3−イル)アセトアミド)フェニル基、4−(2−(メチル(ピリジン−3−イルメチル)アミノ)アセトアミド)フェニル基、4−(3−(N−モルホリニル)プロパンアミド)フェニル基、4−(3−ブロモプロパンアミド)フェニル基、4−(2−(チオフェン−2−イル)アセトアミド)フェニル基、4−(2−(2−オキソピロリジン−1−イル)アセトアミド)フェニル基、4−(2−(2−オキソオキサゾリジン−3−イル)アセトアミド)フェニル基、4−((ジメチルアミノエチル)アミノメチル)フェニル基、4−((メトキシカルボニル)エチル)フェニル基、4−((3−(ジエチルアミノ)ピロリジン−1−イル)メチル)フェニル基、2−(エトキシメチル)フェニル基、4−((N−(tert−ブトキシカルボニル)ピペリジン−4−イル)カルボキサミド)フェニル基、4−(2−(ピロリジン−1−イル)アセトアミド)フェニル基、4−(2−(1H−ピラゾール−1−イル)エトキシ)フェニル基、2−(3−ヒドロキシプロピルアミノ)フェニル基、4−(3−ヒドロキシプロピルアミノ)フェニル基、4−(2−アミノアセトアミド)フェニル基、4−((N−メチルピペリジン−4−イル)カルボキサミド)フェニル基、4−(2−ヒドロキシアセトアミド)フェニル基、2−(ヒドロキシエチルアミノ)フェニル基、2−(ビス(ヒドロキシエチル)アミノ)フェニル基、4−(ヒドロキシエチルアミノ)フェニル基、4−(ビス(ヒドロキシエチル)アミノ)フェニル基、4−(ビス(ヒドロキシプロピル)アミノ)フェニル基又は4−(((1,1−ジオキソ)テトラヒドロチエン−3−イル)(メチル)アミノアセトアミド)フェニル基、である、項目1記載の化合物。
(項目9)
R 3 がチオアニソール−4−イル基、4−(N’−メタンスルホニル)ピペリジニルフェニル基、4−ビス(メタンスルホニル)アミノフェニル基、4−メトキシ−3−(メチルアミノ)フェニル基、4−メトキシ−3−アセトキシフェニル基、4−メトキシ−3−アセトアミドフェニル基、4−メトキシ−3−(メチルオキシカルボニルアミノ)フェニル基(4−メトキシ−3−(methyoxyカルボニルアミノ)フェニル基)、4−メトキシ−3−(シクロプロパンカルボキサミド)フェニル基、4−メトキシ−3−(シクロプロパンカルボキシ)フェニル基、4−メトキシ−3−((エチルアミノ)カルボニル)アミノフェニル基、4−メトキシ−3−アミノフェニル基、4−メトキシ−3−エチルカルボキシフェニル基、3−アミノフェニル基、4−(メタンスルホニル)アミノフェニル基、4−アミノフェニル基、3−ビス(メタンスルホニル)アミノフェニル基、3−(メタンスルホニル)アミノフェニル基、2−オキソ−2,3−ジヒドロベンゾイミダゾール−5−イル基、4−(ピロリジン−1−イルスルホニル)フェニル基、4−アミノ−3−ブロモフェニル基、4−アミノ−3−ヒドロキシフェニル基、4−アミノ−2−ヒドロキシフェニル基、4−((メタンスルホニル)メチルスルホニル)アミノフェニル基、4−アミノ−3−メトキシフェニル基、4−(N’−メチル)ピペラジニルフェニル基、メタンスルホニル基、ピペリジン−4−イル基、1−(tert−ブトキシカルボニル)ピペリジン−4−イル基又は1−(メタンスルホニル)ピペリジン−4−イル基、である、項目7記載の化合物。
(項目10)
L 1 がアルキル基である、項目1記載の化合物。
(項目11)
R a が、1〜3個の置換基で任意に置換されてもよいフェニル基である、項目10記載の化合物。
(項目12)
L 1 がメチル基であり、R a が少なくとも1個の置換基を有するフェニル基である、項目11記載の化合物。
(項目13)
R 2 が4−アセトキシベンジル基、4−ヒドロキシベンジル基、3−ヒドロキシベンジル基、2−(2−イミダゾール−N−イル)アセトアミドベンジル基、2−アセトアミドベンジル基、2−アミノベンジル基、2−ニトロベンジル基、4−((2−イミダゾール−N−イル)アセトアミド)ベンジル基、4−(2−ブロモ)アセトアミドベンジル基、4−アミノベンジル基、3−(2−ピロリジン−N−イル)アセトアミドベンジル基、3−(2−モルホリン−N−イル)アセトアミドベンジル基、3−(2−(N’−メチル)ピペラジン−N−イル)アセトアミドベンジル基、3−(2−((2−ヒドロキシエチル)(メチル)アミノ)アセトアミド)ベンジル基、3−(2−イミダゾール−N−イル)アセトアミドベンジル基、3−((2−ブロモ)アセトアミド)ベンジル基、3−(2−ジメチルアミノ)アセトアミドベンジル基、3−アセトアミドベンジル基、3−アミノベンジル基、4−メタンスルホニルオキシベンジル基、3−(2−アミノ)アセトアミドベンジル基、4−アセトアミドベンジル基、3−(クロロメチル)ベンジル基、3−(ヒドロキシメチル)ベンジル基又は3−(アセトキシメチル)ベンジル基、である、項目12記載の化合物。
(項目14)
R 3 が4−(ビス(メタンスルホニル)アミノ)フェニル基である、項目13記載の化合物。
(項目15)
L 1 がエチル基であり、R a がピペリジニル基、ピロリジニル基、フリル基、チエニル基又はモルホリニル基である、項目14記載の化合物。
(項目16)
R 2 が2−モルホリノエチル基である、項目15記載の化合物。
(項目17)
R b がフェニル基である、項目1記載の化合物。
(項目18)
L 2 が結合であり、
R c がシクロアルキル基、ヘテロシクロアルキル基、アリール基、ヘテロアリール基、(シクロアルキル)アルキル基、(ヘテロシクロアルキル)アルキル基、アラルキル基又はヘテロアラルキル基である、項目17記載の化合物。
(項目19)
L 2 が結合であり、
R c がヘテロシクロアルキル基、ヘテロアリール基、(ヘテロシクロアルキル)アルキル基又はヘテロアラルキル基である、項目17記載の化合物。
(項目20)
L 2 は結合であり、
R c が、テトラゾリル基、モリホリノ基又はピペラジニル基であって、かつ任意に置換されてもよい、項目17記載の化合物。
(項目21)
L 2 が−O−、−S−、−SO 2 −、−CO−、−CO−O−、−NR x −、−NR x −CO−、−NR x −SO 2 −、−NR x −CO−O−、−NR x −CO−NR y −又は−NR x −CO−CO−O−である、項目17記載の化合物。
(項目22)
L 2 が−CO−O−、−NR x −、−NR x −SO 2 −、−NR x −CO−O−又は−NR x −CO−NR y −であって、
かつR x が水素、アルキル基、−CO−アルキル基、−SO 2 −アルキル基、−SO 2 −ヘテロアリール基又は−SO 2 −アリール基である、項目21記載の化合物。
(項目23)
R c が水素、アルキル基、アリール基又はヘテロアリール基である、項目22記載の化合物。
(項目24)
R x が水素、アルキル基、−CO−アルキル基又は−SO 2 −アルキル基であり、
R c が水素、アルキル基又はアリール基である、項目22記載の化合物。
(項目25)
R b が、各々独立に−NRR’及び−C(O)ORからなる群から選択される1〜3個の置換基で置換されたフェニル基であり、
L 2 が結合であり、
R c が水素である、項目1記載の化合物。
(項目26)
L 1 が結合であり、
R a がシクロヘプチル基、ピリジニル基、ピリミジニル基又はフェニル基である、項目1記載の化合物。
(項目27)
R a がシクロヘプチル基である、項目26記載の化合物。
(項目28)
R 3 が4−(エトキシカルボニル)メチルフェニル基、4−(1−メチルピペリジン−4−イル)メチルフェニル基、4−カルボキシメチルフェニル基、((4−エチルピペリジン−1−イル)カルボニル)メチルフェニル基、4−((メチルカルボキサミド)メチル)フェニル基、4−((イソプロピルカルボキサミド)メチル)フェニル基、4−((エトキシカルボニル)イソプロピル)フェニル基、4−(カルボキシイソプロピル)フェニル基、4−(4−メチルピペラジン−1−イル)カルボニル)イソプロピルフェニル基、4−(メタンスルホニル)メチルフェニル基、3−クロロ−4−(メタンスルホニル)メチルフェニル基、4−(メタンスルホニル)(2−モルホリノエチル)アミノフェニル基、4−(メタンスルホニル)(2−ピペリジノエチル)アミノフェニル基、4−(メタンスルホニル)(2−ヒドロキシエチル)アミノフェニル基、4−(メタンスルホニル)イソプロピルアミノフェニル基、4−(メタンスルホニル)(2−ヒドロキシ−3−(ピペリジン−1−イル)プロピル)アミノフェニル基、4−(メタンスルホニル)(2−(ピロリジン−1−イル)エチル)アミノフェニル基、4−(プロパンスルホニル)カルバモイルフェニル基、4−(tert−ブタンスルホニル)カルバモイルフェニル基又は4−(エタンスルホニル)カルバモイルフェニル基である、項目27記載の化合物。
(項目29)
L 1 が結合であり、
R a がシクロヘプチル基、ピリジニル基、ピリミジニル基又はフェニル基であり、
R b がフェニル基であり、
L 2 が結合であり、
R c がシクロアルキル基、ヘテロシクロアルキル基、アリール基、ヘテロアリール基、シクロアルキルアルキル基、ヘテロシクロアルキル基−アルキル基、アラルキル基又はヘテロアラルキル基である、項目3記載の化合物。
(項目30)
L 1 が結合であり、
R a がシクロヘプチル基又はフェニル基であり、
R b がフェニル基であり、
L 2 が結合であり、
R c がテトラゾリル基、モリホリノ基又はピペラジニル基であって、かつ任意に置換されてもよい、項目3記載の化合物。
(項目31)
R a が、パラ位に少なくとも1個の置換基を有するフェニル基である、項目30記載の化合物。
(項目32)
R a がp−メトキシフェニル基又はp−ヒドロキシフェニル基である、項目31記載の化合物。
(項目33)
L 1 が結合であり、
R a が、アルコキシル基で置換されたシクロヘプチル基、ピリジニル基、ピリミジニル基又はフェニル基であり、
R b がフェニル基であり、
L 2 が−O−、−S−、−SO 2 −、−CO−、−CO−O−、−NR x −、−NR x −CO−、−NR x −SO 2 −、−NR x −CO−O−、−NR x −CO−NR y −又は−NR x −CO−CO−O−であって、
かつR x が水素、アルキル基、−CO−アルキル基、−SO 2 −アルキル基又は−SO 2 −アリール基であり、
R c が水素、アルキル基又はアリール基である、項目3記載の化合物。
(項目34)
L 1 が結合であり、R a がシクロヘプチル基又はフェニル基であり、
R b がフェニル基であり、
L 2 が−CO−O−、−NR x −、−NR x −SO 2 −、−NR x −CO−O−又は−NR x −CO−NR y −であって、
かつR x が水素、アルキル基、−CO−アルキル基、−SO 2 −アルキル基又は−SO 2 −アリール基であり、
R c が水素、アルキル基又はアリール基である、項目3記載の化合物。
(項目35)
R x が−SO 2 −アルキル基であり、
R c がアルキル基である、項目34記載の化合物。
(項目36)
R a が、パラ位に少なくとも1個の置換基を有するフェニル基である、項目34記載の化合物。
(項目37)
R a がp−メトキシフェニル基又はp−ヒドロキシフェニル基である、項目36記載の化合物。
(項目38)
L 1 がアルキル基であり、
R a がフェニル基であり、
R b がフェニル基であり、
L 2 が−CO−O−、−NR x −、−NR x −SO 2 −、−NR x −CO−O−又は−NR x −CO−NR y であって、
かつR x 及びR y が各々独立に、水素、アルキル基、−CO−アルキル基、−SO 2 −アルキル基又は−SO 2 −アリール基であり、
R c が水素、アルキル基又はアリール基である、項目3記載の化合物。
(項目39)
L 1 が、フェニル基で置換されたメチル基である、項目38記載の化合物。
(項目40)
L 1 がメチル基であり、
R x が−SO 2 −アルキル基であり、
R c が任意に置換されてもよいアルキル基である、項目38記載の化合物。
(項目41)
R b がフェニル基であり、
L 2 が結合であるか、又は−NR x −SO 2 −であり、
R x が水素であるか、又は−SO 2 −アルキル基であり、
R c が水素、アルキル基、ヘテロシクロアルキル基、ヘテロアリール基、(ヘテロシクロアルキル)アルキル基又はヘテロアラルキル基である、項目1記載の化合物。
(項目42)
R x が−SO 2 −アルキル基であり、
R c がアルキル基である、項目41記載の化合物。
(項目43)
R a が、1〜3個の置換基で任意に置換されてもよいシクロヘキシル基である、項目1記載の化合物。
(項目44)
任意の前記置換基が、アルコキシカルボニル基、ヒドロキシアルキル基、ヒドロキシカルボニル基、アルコキシカルボニルアミノ基及びヒドロキシカルボニルアミノ基、からなる群から各々選択される、項目43記載の化合物。
(項目45)
R a がエトキシカルボニル基、ヒドロキシメチル基、ヒドロキシカルボニル基又はtert−ブトキシカルボニルアミノ基である、項目44記載の化合物。
(項目46)
R 3 が4−(4−メチルピペラジン−1−イル)フェニル)基、4−(ピペラジン−1−イル)フェニル基、4−アミノフェニル基、4−安息香酸基、4−モルホリノフェニル基、4−N,N−ジメチルスルホニルフェニル基又は4−(メタンスルホンアミド)フェニル基である、項目1記載の化合物。
(項目47)
前記化合物が、
N−(4−(1−(3−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)−N−(メチルスルホニル)メタンスルホンアミド、N−(4−(1−(4−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)−N−(メチルスルホニル)メタンスルホンアミド、N−(4−(1−(4−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)シクロプロパンスルホンアミド、1−(4−メトキシフェニル)−N−(3−(4−メチルピペラジン−1−イル)フェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、2−ヒドロキシ−5−(1−(4−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)ベンズアルデヒド、エチル2−(4−(1−(4−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニルアミノ)−2−オキソアセテート、N−(2,3,5,6,8,9,11,12,14,15−デカヒドロベンゾ[b]−[1,4,7,10,13,16]ヘキサオキサシクロオクタデシン−18−イル)−1−(4−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、1−(4−メトキシフェニル)−N−(2,3,5,6,8,9,11,12−オクタヒドロベンゾ[b]−[1,4,7,10,13]ペンタオキサシクロペンタデシン−15−イル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、N−(4−(1−(4−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)−1−(メチルスルホニル)メタンスルホンアミド、3,3,3−トリフルオロ−N−(4−(1−(4−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)プロパン−1−スルホンアミド、1−(4−メトキシフェニル)−N−(4−モルホリノフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、N−(4−(1H−1,2,4−トリアゾール−1−イル)フェニル)−1−(4−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、2−メトキシ−4−(1−(4−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェノール、N−(3,4−ジメトキシフェニル)−1−(4−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、1−(3−(1−(4−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)エタノール、N 1 −(1−(4−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イル)ベンゼン−1,4−ジアミン、N−(4−(1−(4−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)メタンスルホンアミド、4−(1−(4−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェノール、1−(4−メトキシフェニル)−N−(3,4,5−トリメトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、1−(4−メトキシフェニル)−N−(4−(4−(メチルスルホニル)ピペラジン−1−イル)フェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、メチル−3−(4−(1−(4−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニルアミノ)−3−オキソプロパノエート、2−メトキシ−N−(4−(1−(4−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)アセトアミド、N−(3,4−ジヒドロ−2H−ベンゾ[b][1,4]ジオキセピン−7−イル)−1−(4−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、2−エトキシ−5−(1−(4−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェノール、2−(4−(1−(4−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)エタノール、N−(4−(1−(4−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)アセトアミド、2−(2−メトキシエトキシ)−N−(4−(1−(4−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)アセトアミド、ジエチル4−(1−(4−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)ベンジルホスホネート、1−(3−メトキシフェニル)−N−(4−(4−(メチルスルホニル)ピペラジン−1−イル)フェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、ジメチル−4−(1−(4−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニルホスホロアミデート、N 1 −(1−(3−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イル)ベンゼン−1,4−ジアミン、1−(4−メトキシフェニル)−N−(4−(4−メチルピペラジン−1−イル)フェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、N−(3−メトキシフェニル)−1−(4−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、3−(1−(4−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェノール、1−(4−メトキシフェニル)−N−(4−(ピペリジン−1−イル)フェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、N 1 −ビス(4−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、メチル−4−(1−(4−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニルカルバメート、2−(4−(1−(4−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニルアミノ)−2−オキソエチルアセテート、N−(2,3−ジヒドロベンゾ[b][1,4]ダイオキシン−6−イル)−1−(4−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、2−メトキシ−5−(1−(4−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェノール、1−(4−メトキシフェニル)−N−(4−(メチルチオ)フェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、4−(1−(4−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)−2−メチルフェノール、2−メトキシ−4−(1−(3−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェノール、N−(3,4−ジメトキシフェニル)−1−(3−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、2−(2−メトキシエトキシ)−N−(4−(1−(4−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)アセトアミド、(E)−N’−(4−(1−(4−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)−N,N−ジメチルホルムイミダミド、2−メトキシ−5−(1−(3−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェノール、N−(2,2−ジメチルベンゾ[d][1,3]ジオキソール−5−イル)−1−(4−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、メチル2−ヒドロキシ−5−(1−(4−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)ベンゾアート、1−(4−メトキシフェニル)−N−(4−(メチルスルホニル)フェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、3−(1−(3−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェノール、1−(3−メトキシフェニル)−N−(2,3,5,6,8,9,11,12−オクタヒドロベンゾ[b]−[1,4,7,10,13]ペンタオキサシクロペンタデシン−15−イル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、N−(ベンゾ[d][1,3]ジオキソール−5−イル)−1−(3−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、N−(4−(1−(4−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)−N−メチルメタンスルホンアミド、4−メトキシ−N−(4−(1−(4−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)ベンズアミド、N−(2,4−ジメトキシフェニル)−1−(3−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、1−(4−メトキシフェニル)−N−(ナフタレン−1−イル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、N−(4−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)−N−(メチルスルホニル)メタンスルホンアミド、N−(4−(1H−テトラゾール−5−イル)フェニル)−1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、N,N−ジメチル−4−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニルスルファミド、N 1 −(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イル)ベンゼン−1,4−ジアミン、3−クロロ−N−(4−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)プロパン−1−スルホンアミド、3−クロロ−N−(4−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)−プロピル−1,3−スルタム、1−シクロヘプチル−N−(4−(4−(メチルスルホニル)ピペラジン−1−イル)フェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、4−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)安息香酸、1−シクロヘプチル−N−(4−モルホリノフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、3−クロロ−N−(3−クロロプロピルスルホニル)−N−(4−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)プロパン−1−スルホンアミド、(4−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)(モリホリノ)メタノン、N 1 −(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イル)ベンゼン−1,3−ジアミン、1−(4−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)グアニジン、N−(4−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)メタンスルホンアミド、ジメチル−4−(4−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)ピペラジン−1−イルホスホネート、(4−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)(4−エチルピペラジン−1−イル)メタノン、1−シクロヘプチル−N−(4−チオモルホリノフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、ジメチル−4−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニルホスホロアミデート、1−シクロヘプチル−N−(4−(ピペラジン−1−イル)フェニル)−1H−ピラゾロ[3,4−d]ピリミジン−
6−アミン、1−シクロヘプチル−N−(4−(1−メチル−1H−テトラゾール−5−イル)
フェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、2−(4−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)エタノール、1−アリル−3−(4−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)尿素、N−(4−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)アセトアミド、1−(4−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)−3−エチル尿素、1−(4−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)−3−プロピル尿素、1−シクロヘプチル−N−(4−(4−メチルピペラジン−1−イル)フェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、1−シクロヘプチル−N−(4−(2−メチル−2H−テトラゾール−5−イル)フェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、N−(4−(2−(2−クロロエチル)−2H−テトラゾール−5−イル)フェニル)−1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、N−(4−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)チオフェン−2−スルホンアミド、4−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)ベンゾニトリル、N−(3−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)−N−(メチルスルホニル)メタンスルホンアミド、1−シクロヘプチル−N−(4−(ピペリジン−1−イル)フェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、N−(4−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)−1−(メチルスルホニル)−N−(メチルスルホニルメチルスルホニル)メタンスルホンアミド、1−シクロヘプチル−N−(4−(2−モルホリノエトキシ)フェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、N−(4−(1H−ピラゾール−1−イル)フェニル)−1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、N−(4−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)−N−(フェニルスルホニル)ベンゼンスルホンアミド、N−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イル)−1,1,1−トリフルオロ−N−(4−(1,1,1−トリフルオロ−N−(トリフルオロメチルスルホニル)メチルスルホンアミド)フェニル)メタン−スルホンアミド、N−(ベンゾ[d][1,3]ジオキソール−5−イル)−1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、2−(4−(4−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)ピペラジン−1−イル)エタノール、1−シクロヘプチル−N−フェニル−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、1−シクロヘプチル−N−(4−(2−ビニル−2H−テトラゾール−5−イル)フェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、エチル4−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)ベンゾアート、tert−ブチル4−(4−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)ピペラジン−1−カルボキシレート、N−(4−(1−(4−メトキシ−2−メチルフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)−N−(メチルスルホニル)メタンスルホンアミド、1−(4−メトキシ−2−メチルフェニル)−N−(4−(4−(メチルスルホニル)ピペラジン−1−イル)フェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、1−(4−メトキシ−2−メチルフェニル)−N−(4−(4−メチルピペラジン−1−イル)フェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、N−(4−(1−(4−メトキシ−2−メチルフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)メタンスルホンアミド、1−(4−メトキシ−2−メチルフェニル)−N−(4−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、1−(4−メトキシ−2−メチルフェニル)−N−(4−(トリフルオロメトキシ)フェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、1−(4−メトキシ−2−メチルフェニル)−N−(4−(メチルチオ)フェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、2−メトキシ−5−(1−(4−メトキシ−2−メチルフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェノール、3−(6−(4−アミノフェニルアミノ)−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)フェノール、4−(6−(4−アミノフェニルアミノ)−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)フェノール、4−(6−(4−モルホリノフェニルアミノ)−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)フェノール、5−(1−(3−ヒドロキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)−2−メトキシフェノール、5−(1−(4−ヒドロキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)−2−メトキシフェノール、N 1 −(1−(4−ヨードフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イル)ベンゼン−1,4−ジアミン、4−(4−(6−(4−アミノフェニルアミノ)−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)フェニル)ブト−3−イン−1−オール、4−(4−(6−(3,4−ジメトキシフェニルアミノ)−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)フェニル)ブト−3−イン−1−オール、N−(3,4−ジメトキシフェニル)−1−(4−ヨードフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、5−(1−(4−ヨードフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)−2−メトキシフェノール、1−(4−エチルフェニル)−N−(4−(ピペリジン−1−イル)フェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、1−(4−ヨードフェニル)−N−(4−(ピペリジン−1−イル)フェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、1−ベンジル−N−(4−(ピペリジン−1−イル)フェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、1−(3−メトキシベンジル)−N−(4−(ピペラジン−1−イル)フェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、1−(3,4−ジメトキシベンジル)−N−(4−(ピペラジン−1−イル)フェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、tert−ブチル4−(4−(1−(3,5−ジメトキシベンジル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)ピペラジン−1−カルボキシレート、1−(3,5−ジメトキシベンジル)−N−(4−(ピペラジン−1−イル)フェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、tert−ブチル4−(4−(3−ブロモ−1−(3,4−ジメトキシベンジル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)ピペラジン−1−カルボキシレート、tert−ブチル4−(4−(1−(3,4−ジメトキシベンジル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)ピペラジン−1−カルボキシレート、1−(4−メトキシベンジル)−N−(4−(ピペラジン−1−イル)フェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、tert−ブチル4−(4−(1−(4−メトキシベンジル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)ピペラジン−1−カルボキシレート、1−(2,3−ジヒドロ−1H−インデン−2−イル)−N−(4−モルホリノフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、エチル2−(4−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)アセテート、1−シクロヘプチル−N−(4−((4−メチルピペラジン−1−イル)メチル)フェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、2−(4−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)酢酸、2−(4−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)−1−(4−エチルピペラジン−1−イル)エタノン、2−(4−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)−N−メチルアセトアミド、2−(4−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)−N−イソプロピルアセトアミド、エチル2−(4−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)−2−メチルプロパノエート、2−(4−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)−2−メチルプロパン酸、エチル2−(2−クロロ−4−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)アセテート、2−(2−クロロ−4−(1−シクロヘプチル−1H−ピラゾロ[3,4d]ピリミジン−6−イルアミノ)フェニル)酢酸、2−(4−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)−2−メチル−1−(4−メチルピペラジン−1−イル)プロパン−1−オン、1−シクロヘプチル−N−(4−(メチルスルホニルメチル)フェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、N−(3−クロロ−4−(メチルスルホニルメチル)フェニル)−1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、N−(4−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)−N−(2−モルホリノエチル)メタンスルホンアミド、N−(4−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)−N−(2−(ピペリジン−1−イル)エチル)メタンスルホンアミド、N−(4−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)−N−(2−ヒドロキシエチル)メタンスルホンアミド、N−(4−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)−N−イソプロピルメタンスルホンアミド、N−(4−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)−N−(2−ヒドロキシ−3−(ピペリジン−1−イル)プロピル)メタンスルホンアミド、N−(4−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)−N−(2−(ピロリジン−1−イル)エチル)メタンスルホンアミド、N−(4−(1−(4−ヒドロキシ−2,3−ジヒドロ−1H−インデン−1−イル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)−N−(メチルスルホニル)メタンスルホンアミド、(S)−N−(4−(1−(2,3−ジヒドロ−1H−インデン−1−イル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)−N−(エチルスルホニル)エタンスルホンアミド、1−(6−(4−(4−メチルピペラジン−1−イル)フェニルアミノ)−1H−ピラゾロ[3,4−d]ピリミ
ジン−1−イル)
−2,3−ジヒドロ−1H−インデン−4−オール、1−(6−(4−(N−(メチルスルホニル)メチルスルホンアミド)フェニルアミノ)−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)−2,3−ジヒドロ−1H−インデン−4−イルベンゾアート、1−(6−(4−(N−(メチルスルホニル)メチルスルホンアミド)フェニルアミノ)−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)−2,3−ジヒドロ−1H−インデン−4−イル二水素ホスフェート、(S)−1−クロロ−N−(クロロメチルスルホニル)−N−(4−(1−(2,3−ジヒドロ−1H−インデン−1−イル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)メタンスルホンアミド、N−(4−(1−(6,7−ジヒドロ−5H−インデノ[5,6−d][1,3]ジオキソール−5−イル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)−N−(メチルスルホニル)メタンスルホンアミド、N−(1−(6−(4−(N−(メチルスルホニル)メチルスルホンアミド)フェニルアミノ)−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)−2,3−ジヒドロ−1H−インデン−5−イル)アセトアミド、N−(4−(1−(4−ヒドロキシ−2,3−ジヒドロ−1H−インデン−1−イル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)メタンスルホンアミド、1−(6−(4−(N−(メチルスルホニル)メチルスルホンアミド)フェニルアミノ)−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)−2,3−ジヒドロ−1H−インデン−5−イルベンゾアート、(S,Z)−4−(1−(2,3−ジヒドロ−1H−インデン−1−イル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)−N’−ヒドロキシベンズイミドアミド、1−(6−(4−(4−メチルピペラジン−1−イル)フェニルアミノ)−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)−2,3−ジヒドロ−1H−インデン−4−イルベンゾアート、1−(6−(4−アミノフェニルアミノ)−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)−2,3−ジヒドロ−1H−インデン−4−オール、1−(6−(4−アミノフェニルアミノ)−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)−2,3−ジヒドロ−1H−インデン−4−イルベンゾアート、ジ−tert−ブチル1−(6−(4−(N−(メチルスルホニル)メチルスルホンアミド)フェニルアミノ)−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)−2,3−ジヒドロ−1H−インデン−4−イルホスフェート、(S)−4−(1−(2,3−ジヒドロ−1H−インデン−1−イル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)−N−(メチルスルホニル)ベンズアミド、N−(4−(1−(5−((2−メトキシエトキシ)メトキシ)−2,3−ジヒドロ−1H−インデン−1−イル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)−N−(メチルスルホニル)メタンスルホンアミド、N−(1−(6−(4−アミノフェニルアミノ)−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)−2,3−ジヒドロ−1H−インデン−5−イル)アセトアミド、(S)−4−(1−(2,3−ジヒドロ−1H−インデン−1−イル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)ベンゾニトリル、(S)−N−(4−(1H−テトラゾール−5−イル)フェニル)−1−(2,3−ジヒドロ−1H−インデン−1−イル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、N1−(1−(5−メトキシ−2,3−ジヒドロ−1H−インデン−1−イル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イル)ベンゼン−1,4−ジアミン、N−(4−(1−(5−メトキシ−2,3−ジヒドロ−1H−インデン−1−イル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)−N−(メチルスルホニル)メタンスルホンアミド、(S)−1−(2,3−ジヒドロ−1H−インデン−1−イル)−N−(4−ニトロフェネチル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、(S)−N−(4−アミノフェネチル)−1−(2,3−ジヒドロ−1H−インデン−1−イル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、(S)−N−(4−(2−(1−(2,3−ジヒドロ−1H−インデン−1−イル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)エチル)フェニル)−N−(メチルスルホニル)メタンスルホンアミド、N−(4−(1−(1H−インドール−4−イル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)−N−(メチルスルホニル)メタンスルホンアミド、N−(4−(1−(1H−インドール−6−イル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)−N−(メチルスルホニル)メタンスルホンアミド、N−(4−(1−(1H−インドール−5−イル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)−N−(メチルスルホニル)メタンスルホンアミド、N−(4−(1−(ベンゾ[d][1,3]ジオキソール−5−イル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)−N−(メチルスルホニル)メタンスルホンアミド、1−(1H−インドール−4−イル)−N−(4−(4−メチルピペラジン−1−イル)フェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、N−(4−(1−(1−メチル−1H−インドール−5−イル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)−N−(メチルスルホニル)メタンスルホンアミド、1−(7−メチル−1H−インドール−4−イル)−N−(4−(4−メチルピペラジン−1−イル)フェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、tert−ブチル7−メチル−4−(6−(4−(4−メチルピペラジン−1−イル)フェニルアミノ)−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)−1H−インドール−1−カルボキシレート、tert−ブチル4−(6−(4−(4−メチルピペラジン−1−イル)フェニルアミノ)−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)−1H−インドール−1−カルボキシレート、N−(4−モルホリノフェニル)−1−(ナフタレン−1−イルメチル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、1−ブチル−N−(4−(ピペリジン−1−イル)フェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、1−イソプロピル−N−(4−(ピペリジン−1−イル)フェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、1−(シクロペンチルメチル)−N−(4−(ピペリジン−1−イル)フェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、(S)−N−(4−モルホリノフェニル)−1−(1−フェニルエチル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、1−((6−フルオロ−4H−ベンゾ[d][1,3]ダイオキシン−8−イル)メチル)−N−(4−モルホリノフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、1−(フラン−2−イルメチル)−N−(4−(ピペラジン−1−イル)フェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、エチル2−(6−(4−(ピペリジン−1−イル)フェニルアミノ)−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)アセテート、N−(4−モルホリノフェニル)−1−(ピリジン−2−イルメチル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、1−メチル−N−(4−(ピペリジン−1−イル)フェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、N−(4−モルホリノフェニル)−1−(1,2,3,4−テトラヒドロナフタレン−1−イル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、1−(1−ベンジルピペリジン−4−イル)−N−(4−モルホリノフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、又は、1−((4−メトキシ−3,5−ジメチルピリジン−2−イル)メチル)−N−(4−モルホリノフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、である、項目1記載の化合物。
(項目48)
前記化合物が、
N−(4−(1H−テトラゾール−5−イル)フェニル)−1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、N−(4−(1H−テトラゾール−5−イル)フェニル)−1−(ビフェニル−2−イル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、N−(4−(1H−テトラゾール−5−イル)フェニル)−1−(3−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、N−(4−(1H−テトラゾール−5−イル)フェニル)−1−(4−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、1−シクロヘプチル−N−(4−モルホリノフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、1−(ビフェニル−2−イル)−N−(4−モルホリノフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、N−(4−モルホリノフェニル)−1−(フェナントレン−4−イル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、1−(3−メトキシフェニル)−N−(4−モルホリノフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、1−(4−メトキシフェニル)−N−(4−モルホリノフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、1−シクロヘプチル−N−(4−(ピペラジン−1−イル)フェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、1−(ビフェニル−2−イル)−N−(4−(ピペラジン−1−イル)フェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、1−(3−メトキシフェニル)−N−(4−(ピペラジン−1−イル)フェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、1−(4−メトキシフェニル)−N−(4−(ピペラジン−1−イル)フェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、4−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)安息香酸、4−(1−(ビフェニル−2−イル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)安息香酸、4−(1−(3−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)安息香酸、4−(1−(4−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)安息香酸、N 1 −(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イル)ベンゼン−1,4−ジアミン、N 1 −(1−(ビフェニル−2−イル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イル)ベンゼン−1,4−ジアミン、N 1 −(1−(3−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イル)ベンゼン−1,4−ジアミン、N 1 −(1−(4−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イル)ベンゼン−1,4−ジアミン、N−(4−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)−N−(メチルスルホニル)メタンスルホンアミド、N−(4−(1−(ビフェニル−2−イル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)−N−(メチルスルホニル)メタンスルホンアミド、N−(4−(1−(3−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)−N−(メチルスルホニル)メタンスルホンアミド、N−(4−(1−(4−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)−N−(メチルスルホニル)メタンスルホンアミド、N−(4−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)メタンスルホンアミド、N−(4−(1−(ビフェニル−2−イル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)メタンスルホンアミド、N−(4−(1−(フェナントレン−4−イル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)メタンスルホンアミド、N−(4−(1−(3−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)メタンスルホンアミド、N−(4−(1−(4−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)メタンスルホンアミド、1−シクロヘプチル−N−(4−(4−メチルピペラジン−1−イル)フェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、1−(ビフェニル−2−イル)−N−(4−(4−メチルピペラジン−1−イル)フェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、1−(3−メトキシフェニル)−N−(4−(4−メチルピペラジン−1−イル)フェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、1−(4−メトキシフェニル)−N−(4−(4−メチルピペラジン−1−イル)フェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、5−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)−2−メトキシフェノール、5−(1−(ビフェニル−2−イル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)−2−メトキシフェノール、2−メトキシ−5−(1−(3−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェノール、4−(6−(4−(N−(メチルスルホニル)メチルスルホンアミド)フェニルアミノ)−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)フェニル二水素ホスフェート4−メトキシ−N1−(1−(4−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イル)ベンゼン−1,3−ジアミン4−(6−(4−(N−(メチルスルホニル)メチルスルホンアミド)フェニルアミノ)−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)フェニルアセテート4−(6−(4−(N−(メチルスルホニル)メチルスルホンアミド)フェニルアミノ)−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)フェニルスルファメートN−(4−(1−(4−ヒドロキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)−N−(メチルスルホニル)メタンスルホンアミド、2−メトキシ−5−(1−(4−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェノール、1−(シクロペンチルメチル)−N−(4−(ピペリジン−1−イル)フェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、(S)−N−(4−モルホリノフェニル)−1−(1−フェニルエチル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、1−((6−フルオロ−4H−ベンゾ[d][1,3]ダイオキシン−8−イル)メチル)−N−(4−モルホリノフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、1−(フラン−2−イルメチル)−N−(4−(ピペラジン−1−イル)フェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、N−(4−モルホリノフェニル)−1−(ピリジン−2−イルメチル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、1−(1−ベンジルピペリジン−4−イル)−N−(4−モルホリノフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、1−((4−メトキシ−3,5−ジメチルピリジン−2−イル)メチル)−N−(4−モルホリノフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、N−(5−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)ピリジン−2−イル)−N−(メチルスルホニル)メタンスルホンアミド、N−(5−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)ピリジン−2−イル)メタンスルホンアミド、N−(5−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)ピリジン−2−イル)−N−(2−ヒドロキシエチル)メタンスルホンアミド、N−(4−(6−(6−(N−(メチルスルホニル)メチルスルホンアミド)ピリジン−3−イルアミノ)−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)フェニル)−2−(ピロリジン−1−イル)アセトアミド、N−(4−(6−(6−(メチルスルホンアミド)ピリジン−3−イルアミノ)−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)フェニル)−2−(ピロリジン−1−イル)アセトアミド、N−(5−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)ピリジン−2−イル)−N−(2−モルホリノエチル)メタンスルホンアミド、N−(5−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)ピリジン−2−イル)−N−(2,3−ジヒドロキシプロピル)メタンスルホンアミド、N−(4−(6−(6−(N−(2,3−ジヒドロキシプロピル)メチルスルホンアミド)ピリジン−3−イルアミノ)−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)フェニル)−2−(ピロリジン−1−イル)アセトアミド、tert−ブチル4−(6−(6−(N−(2,3−ジヒドロキシプロピル)メチルスルホンアミド)ピリジン−3−イルアミノ)−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)フェニルカルバメート、tert−ブチル4−(6−(6−(N−(2−モルホリノエチル)メチルスルホンアミド)ピリジン−3−イルアミノ)−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)フェニルカルバメート、N−(5−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)ピリミジン−2−イル)メタンスルホンアミド、N−(5−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)ピリミジン−2−イル)−N−(2,3−ジヒドロキシプロピル)メタンスルホンアミド、tert−ブチル4−(6−(2−(N−(2,3−ジヒドロキシプロピル)メチルスルホンアミド)ピリミジン−5−イルアミノ)−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)フェニルカルバメート、N−(5−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)ピリミジン−2−イル)−N−(2−モルホリノエチル)メタンスルホンアミド、N−(4−(6−(2−(N−(2,3−ジヒドロキシプロピル)メチルスルホンアミド)ピリミジン−5−イルアミノ)−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)フェニル)−2−(ピロリジン−1−イル)アセトアミド、tert−ブチル4−(6−(2−(N−(2−モルホリノエチル)メチルスルホンアミド)ピリミジン−5−イルアミノ)−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)フェニルカルバメート、tert−ブチル5−(6−(2−(N−(2−モルホリノエチル)メチルスルホンアミド)ピリミジン−5−イルアミノ)−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)ピリジン−2−イルカルバメート、N−(5−(6−(2−(N−(2,3−ジヒドロキシプロピル)メチルスルホンアミド)ピリミジン−5−イルアミノ)−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)ピリジン−2−イル)−2−(ピロリジン−1−イル)アセトアミド、N−(5−(6−(6−(N−(2,3−ジヒドロキシプロピル)メチルスルホンアミド)ピリジン−3−イルアミノ)−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)ピリジン−2−イル)−2−(ピロリジン−1−イル)アセトアミド、tert−ブチル5−(6−(6−(N−(2−モルホリノエチル)メチルスルホンアミド)ピリジン−3−イルアミノ)−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)ピリジン−2−イルカルバメート、tert−ブチル6−(6−(6−(N−(2−モルホリノエチル)メチルスルホンアミド)ピリ
ジン−3−イルアミノ)−1H−ピラゾロ[3,4−d]ピリミジ
ン−1−イル)ピリジン−3−イルカルバメート、N−(6−(6−(6−(N−(2,3−ジヒドロキシプロピル)メチルスルホンアミド)ピリジン−3−イルアミノ)−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)ピリジン−3−イル)−2−(ピロリジン−1−イル)アセトアミド、tert−ブチル6−(6−(2−(N−(2,3−ジヒドロキシプロピル)メチルスルホンアミド)ピリミジン−5−イルアミノ)−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)ピリジン−3−イルカルバメート、tert−ブチル6−(6−(6−(N−(2,3−ジヒドロキシプロピル)メチルスルホンアミド)ピリジン−3−イルアミノ)−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)ピリジン−3−イルカルバメート、N−(5−(1−(3−ヒドロキシベンジル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)ピリジン−2−イル)メタンスルホンアミド、N−(2,3−ジヒドロキシプロピル)−N−(5−(1−(3−ヒドロキシベンジル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)ピリジン−2−イル)メタンスルホンアミド、N−(2,3−ジヒドロキシプロピル)−N−(5−(1−(2−ヒドロキシピリジン−4−イル)メチル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)ピリジン−2−イル)メタンスルホンアミド、N−(5−(1−(3−ヒドロキシベンジル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)ピリジン−2−イル)−N−(2−モルホリノエチル)メタンスルホンアミド、N−(2,3−ジヒドロキシプロピル)−N−(4−(1−((2−ヒドロキシピリジン−4−イル)メチル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)メタンスルホンアミド、又は、N−(5−(1−((2−ヒドロキシピリジン−4−イル)メチル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)ピリジン−2−イル)−N−(2−モルホリノエチル)メタンスルホンアミド、である、項目1記載の化合物。
(項目49)
項目1から48のいずれか1項記載の化合物と、薬理学的に許容できる担体と、を含んでなる医薬組成物。
(項目50)
プロテインキナーゼで媒介される疾患に罹患する被験者を治療する方法であって、前記被験者に、薬理学的に有効量の、項目1から48のいずれか1項記載の化合物を投与することを含む方法。
(項目51)
細胞内のプロテアーゼキナーゼを阻害する方法であって、項目1から48のいずれか1項記載の化合物と前記細胞とを接触させることを含む方法。
(項目52)
前記プロテアーゼキナーゼが、細胞の有糸***に関与する1つ以上のプロテアーゼキナーゼである、項目51記載の方法。
(項目53)
前記プロテアーゼキナーゼが、オーロラキナーゼ又はサイクリン依存性キナーゼである、項目52記載の方法。
(項目54)
被験者の腫瘍又は癌を治療する方法であって、かかる治療を必要とする被験者に、項目1から48のいずれか1項記載の化合物を投与することを含む方法。
(項目55)
前記腫瘍又は癌が、骨癌、脳及びCNS腫瘍、乳癌、乳癌、結腸直腸癌、内分泌腺の癌、胃腸癌、尿生殖器癌、婦人科癌、頭部及び頸部癌、白血病、肺癌、リンパ腫、眼癌、皮膚癌、軟部組織肉腫、泌尿器系癌、及び他のタイプの若しくは関連する障害である、項目54記載の方法。
本発明は、式(I)の化合物、
For example, the present invention provides the following items.
(Item 1)
A compound of formula (I), a prodrug, polymorph, tautomer, enantiomer, stereoisomer, solvate, N-oxide derivative or pharmaceutically acceptable salt thereof.
(Wherein R 1 Is hydrogen or a halo group,
R 2 Is -L 1 -R a And
L 1 Is a bond or an alkyl group;
R a Is a cyclohexyl group, cycloheptyl group, piperidinyl group, pyrrolidinyl group, furyl group, thienyl group, morpholinyl group, pyridinyl group or pyrimidinyl group, each optionally substituted with 1 to 3 substituents, or ,
R a Is a substituted phenyl group,
R 3 Is -R b -L 2 -R c And
R b Is an aryl group, heteroaryl group, cycloalkyl group or heterocycloalkyl group, which may be optionally substituted with 1 to 3 substituents, and when two of the substituents are adjacent, Together with one or more atoms to which is bonded forms a 5-16 membered ring having 0-6 heterocyclic atoms;
L 2 Is a bond,-(CR x R y ) n -, -N =, -O-, -S-, -SO-, -SO 2 -, -CO-, -CO-O-, -O-CO-, -NR x -, -NR x -CO-, -NR x -SO 2 -, -CO-NR x -, -SO 2 -NR x -, -NR x -CO-O-, -NR x -SO 2 -O-, -NR x -CO-NR y -, -NR x -SO 2 -NR y -, -CO-NR x -NR y -, -SO 2 -NR x -NR y -, -NR x -CO-CO-O-, -NR x -SO 2 -SO 2 -O-, -S (O) 2 -N x -CO-R y -, -CO-N x -S (O) 2 -R y -Or- (NR x R y ) C = N-O-
R c Is hydrogen, alkyl group, alkenyl group, alkynyl group, guanidinyl group, cycloalkyl group, heterocycloalkyl group, cycloalkenyl group, heterocycloalkenyl group, aryl group, heteroaryl group, (cycloalkyl) alkyl group, (heterocyclo An alkyl) alkyl group, a (cycloalkenyl) alkyl group, a (heterocycloalkenyl) alkyl group, an aralkyl group or a heteroaralkyl group, and optionally substituted with 1 to 3 substituents, excluding hydrogen. Well,
R x And R y Are each independently hydrogen, hydroxy group, alkyl group, alkoxy group, amino group, -CO-alkyl group, -CO-aryl group, -SO 2 -Alkyl group, -SO 2 -Aryl group, -SO 2 -Heteroaryl group or -P (O) (O-alkyl) 2 And
R x Or R y The alkyl or aryl moiety of may be optionally substituted with 1 to 3 substituents,
n is 0, 1, 2, or 3)
(Item 2)
R a , R b , R c , R x And R y The above 1-3 optional substituents are each independently an alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, arylalkyl group, heteroarylalkyl. Group, -OR, -SR, -NRR ', oxo group, -C (O) -OR, -C (O) -NRR', halo group, CN, NO 2 , N 3 , -C (O) R ", -P (O) (OR) (OR '), -O-P (O) (OR) (OR'), -NR-P (O) (OR) (OR ' ), -S (O) 2 -OR, -O-S (O) 2 -OR, -NR-S (O) 2 -OR ', -NR-C (O) -OR ", -NR-C (O) -NRR', -NR-C (S) -NRR ', -C (S) -NRR' and a thioalkyl group. ,
R and R ′ are each independently hydrogen, alkyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, aralkyl group or heteroaralkyl group,
The compound according to item 1, wherein R ″ is an alkyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an aralkyl group or a heteroaralkyl group.
(Item 3)
R 1 2. The compound according to item 1, wherein is hydrogen.
(Item 4)
L 1 2. The compound according to item 1, wherein is a bond.
(Item 5)
R a 5. The compound according to item 4, wherein is a cycloheptyl group.
(Item 6)
R a 5. The compound according to item 4, wherein is a phenyl group substituted with 1 to 3 substituents.
(Item 7)
R a 7. The compound according to item 6, wherein is a phenyl group having at least one substituent at the para position.
(Item 8)
R 2 Are 1- (biphenyl-2-yl) group, 4-hydroxyphenyl group, 4- (hydroxymethyl) phenyl group, 3- (hydroxyethyl) phenyl group, 4- (chloromethyl) phenyl group, 4- (tert- Butoxycarbonyl) phenyl group, 2- (tert-butoxycarboxamido) phenyl group, 4- (tert-butoxycarboxamido) phenyl group, 3-methoxyphenyl group, 4-methoxyphenyl group, 3,4-dimethoxyphenyl group, 4- Iodophenyl group, 4-methoxy-2-methylphenyl group, 4-methoxy-3-methylphenyl group, 4-acetylphenyl group, 3-acetylphenyl group, 4- (diethoxyphosphoryloxy) phenyl group, 4-amino Phenyl group, 4-nitrophenyl group, 4-acetamidophenyl group, 3-acetoa Dophenyl group, 2-acetamidophenyl group, 4- (tert-butoxycarboxamido) phenyl group, 4- (dimethylaminoethoxy) phenyl group, 5-methoxy-2,4-dinitrophenyl group, 3-methoxy-2,4- Dinitrophenyl group, 4- (morpholin-4-ylcarbonyl) phenyl group, 4- (dimethylamino) phenyl group, 4-methoxycarbonyl-3-fluorophenyl group, 4- (di (cyclopropylcarbonyl) amino) phenyl group 2-methylthiophenyl group, 2-ethylthiophenyl group, 3- (isopropyloxy) phenyl group, 4-isopropylphenyl group, 4- (methoxyacetamido) phenyl group, 4- (isopropylacetamido) phenyl group, 4- ( Dimethylaminoacetamido) phenyl group, 4-meth Ci-3- (trifluoromethyl) phenyl group, 4- (acrylamide) phenyl group, 4- (di (2-furanylcarboxy) amido) phenyl group, 4- (2-furanyl) carboxamidophenyl group, 4- ( (Ethoxycarbonyl) methylcarboxamido) phenyl group, 4- (cyclopropylcarboxamido) phenyl group, 4- (trifluoromethoxy) phenyl group, 4- (2- (piperidin-1-yl) acetamido) phenyl group, 4- ( (Tert-Butoxycarboxamido) methylcarboxamido) phenyl group, 2-vinylphenyl group, 2- (methylsulfonyl) phenyl group, 4- (2- (2-methyl-imidazol-1-yl) acetamido) phenyl group, 4 -(2- (imidazol-1-yl) acetamido) phenyl group, 4- (2 -(Pyrrolidin-1-yl) acetamido) phenyl group, 4- (3- (pyrrolidin-1-yl) propanamido) phenyl group, 4- (2- (pyrrolidin-1-yl) acetamido) phenyl group, 4- (2- (4-methylpiperazin-1-yl) acetamido) phenyl group, 4- (3- (4-methylpiperazin-1-yl) propanamido) phenyl group, 4- (3- (imidazol-yl) propane Amido) phenyl group, 4-((4-methoxycarbonyl) butanamido) phenyl group, 4-((2-bis (2-hydroxyethyl) amino) acetamido) phenyl group, 4- (cyclohexylcarboxamido) phenyl group, 4- (Bis (cyclohexylcarbonyl) amino) phenyl group, 4-((N-morpholinyl) carboxamido) phenyl group 4- (2- (pyridin-3-yl) acetamido) phenyl group, 4- (2- (methyl (pyridin-3-ylmethyl) amino) acetamido) phenyl group, 4- (3- (N-morpholinyl) propanamide ) Phenyl group, 4- (3-bromopropanamido) phenyl group, 4- (2- (thiophen-2-yl) acetamido) phenyl group, 4- (2- (2-oxopyrrolidin-1-yl) acetamide) Phenyl group, 4- (2- (2-oxooxazolidin-3-yl) acetamido) phenyl group, 4-((dimethylaminoethyl) aminomethyl) phenyl group, 4-((methoxycarbonyl) ethyl) phenyl group, 4 -((3- (diethylamino) pyrrolidin-1-yl) methyl) phenyl group, 2- (ethoxymethyl) phenyl group, 4-((N (Tert-butoxycarbonyl) piperidin-4-yl) carboxamido) phenyl group, 4- (2- (pyrrolidin-1-yl) acetamido) phenyl group, 4- (2- (1H-pyrazol-1-yl) ethoxy) Phenyl group, 2- (3-hydroxypropylamino) phenyl group, 4- (3-hydroxypropylamino) phenyl group, 4- (2-aminoacetamido) phenyl group, 4-((N-methylpiperidin-4-yl) ) Carboxamido) phenyl group, 4- (2-hydroxyacetamido) phenyl group, 2- (hydroxyethylamino) phenyl group, 2- (bis (hydroxyethyl) amino) phenyl group, 4- (hydroxyethylamino) phenyl group, 4- (bis (hydroxyethyl) amino) phenyl group, 4- (bis (hydroxypro 2. The compound according to item 1, which is a pyr) amino) phenyl group or 4-(((1,1-dioxo) tetrahydrothien-3-yl) (methyl) aminoacetamido) phenyl group.
(Item 9)
R 3 Is a thioanisol-4-yl group, 4- (N′-methanesulfonyl) piperidinylphenyl group, 4-bis (methanesulfonyl) aminophenyl group, 4-methoxy-3- (methylamino) phenyl group, 4- Methoxy-3-acetoxyphenyl group, 4-methoxy-3-acetamidophenyl group, 4-methoxy-3- (methyloxycarbonylamino) phenyl group (4-methoxy-3- (methyloxycarbonylamino) phenyl group), 4- Methoxy-3- (cyclopropanecarboxamido) phenyl group, 4-methoxy-3- (cyclopropanecarboxy) phenyl group, 4-methoxy-3-((ethylamino) carbonyl) aminophenyl group, 4-methoxy-3-amino Phenyl group, 4-methoxy-3-ethylcarboxyphenyl group, 3-aminophenyl Enyl group, 4- (methanesulfonyl) aminophenyl group, 4-aminophenyl group, 3-bis (methanesulfonyl) aminophenyl group, 3- (methanesulfonyl) aminophenyl group, 2-oxo-2,3-dihydrobenzo Imidazol-5-yl group, 4- (pyrrolidin-1-ylsulfonyl) phenyl group, 4-amino-3-bromophenyl group, 4-amino-3-hydroxyphenyl group, 4-amino-2-hydroxyphenyl group, 4-((methanesulfonyl) methylsulfonyl) aminophenyl group, 4-amino-3-methoxyphenyl group, 4- (N′-methyl) piperazinylphenyl group, methanesulfonyl group, piperidin-4-yl group, 1 -(Tert-butoxycarbonyl) piperidin-4-yl group or 1- (methanesulfonyl) piperidine-4 The compound according to Item 7, which is an -yl group.
(Item 10)
L 1 2. The compound according to item 1, wherein is an alkyl group.
(Item 11)
R a Item 11. The compound according to Item 10, wherein is a phenyl group which may be optionally substituted with 1 to 3 substituents.
(Item 12)
L 1 Is a methyl group and R a 12. The compound according to item 11, wherein is a phenyl group having at least one substituent.
(Item 13)
R 2 4-acetoxybenzyl group, 4-hydroxybenzyl group, 3-hydroxybenzyl group, 2- (2-imidazol-N-yl) acetamidobenzyl group, 2-acetamidobenzyl group, 2-aminobenzyl group, 2-nitrobenzyl Group, 4-((2-imidazol-N-yl) acetamido) benzyl group, 4- (2-bromo) acetamidobenzyl group, 4-aminobenzyl group, 3- (2-pyrrolidin-N-yl) acetamidobenzyl group , 3- (2-morpholin-N-yl) acetamidobenzyl group, 3- (2- (N′-methyl) piperazin-N-yl) acetamidobenzyl group, 3- (2-((2-hydroxyethyl) ( Methyl) amino) acetamido) benzyl group, 3- (2-imidazol-N-yl) acetamidobenzyl group, 3-((2 -Bromo) acetamido) benzyl group, 3- (2-dimethylamino) acetamidobenzyl group, 3-acetamidobenzyl group, 3-aminobenzyl group, 4-methanesulfonyloxybenzyl group, 3- (2-amino) acetamidobenzyl group 13. The compound according to item 12, which is 4-acetamidobenzyl group, 3- (chloromethyl) benzyl group, 3- (hydroxymethyl) benzyl group or 3- (acetoxymethyl) benzyl group.
(Item 14)
R 3 14. The compound according to item 13, wherein is a 4- (bis (methanesulfonyl) amino) phenyl group.
(Item 15)
L 1 Is an ethyl group and R a 15. The compound according to item 14, wherein is a piperidinyl group, pyrrolidinyl group, furyl group, thienyl group or morpholinyl group.
(Item 16)
R 2 16. The compound according to item 15, wherein is a 2-morpholinoethyl group.
(Item 17)
R b 2. The compound according to item 1, wherein is a phenyl group.
(Item 18)
L 2 Is a bond,
R c 18. The compound according to item 17, wherein is a cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, (cycloalkyl) alkyl group, (heterocycloalkyl) alkyl group, aralkyl group or heteroaralkyl group.
(Item 19)
L 2 Is a bond,
R c 18. The compound according to item 17, wherein is a heterocycloalkyl group, heteroaryl group, (heterocycloalkyl) alkyl group or heteroaralkyl group.
(Item 20)
L 2 Is a bond,
R c 18. The compound according to item 17, wherein is a tetrazolyl group, morpholino group or piperazinyl group, and may be optionally substituted.
(Item 21)
L 2 -O-, -S-, -SO 2 -, -CO-, -CO-O-, -NR x -, -NR x -CO-, -NR x -SO 2 -, -NR x -CO-O-, -NR x -CO-NR y -Or-NR x 18. The compound according to item 17, which is —CO—CO—O—.
(Item 22)
L 2 -CO-O-, -NR x -, -NR x -SO 2 -, -NR x -CO-O- or -NR x -CO-NR y -And
And R x Is hydrogen, an alkyl group, -CO-alkyl group, -SO 2 -Alkyl group, -SO 2 -Heteroaryl group or -SO 2 -The compound according to item 21, which is an aryl group.
(Item 23)
R c 23. A compound according to item 22, wherein is a hydrogen, alkyl group, aryl group or heteroaryl group.
(Item 24)
R x Is hydrogen, an alkyl group, -CO-alkyl group or -SO 2 -An alkyl group,
R c 23. The compound according to item 22, wherein is a hydrogen atom, an alkyl group or an aryl group.
(Item 25)
R b Are each independently a phenyl group substituted with 1 to 3 substituents selected from the group consisting of —NRR ′ and —C (O) OR;
L 2 Is a bond,
R c 2. The compound according to item 1, wherein is hydrogen.
(Item 26)
L 1 Is a bond,
R a 2. The compound according to item 1, wherein is a cycloheptyl group, a pyridinyl group, a pyrimidinyl group or a phenyl group.
(Item 27)
R a 27. The compound according to item 26, wherein is a cycloheptyl group.
(Item 28)
R 3 Are 4- (ethoxycarbonyl) methylphenyl group, 4- (1-methylpiperidin-4-yl) methylphenyl group, 4-carboxymethylphenyl group, ((4-ethylpiperidin-1-yl) carbonyl) methylphenyl group 4-((methylcarboxamido) methyl) phenyl group, 4-((isopropylcarboxamido) methyl) phenyl group, 4-((ethoxycarbonyl) isopropyl) phenyl group, 4- (carboxyisopropyl) phenyl group, 4- (4 -Methylpiperazin-1-yl) carbonyl) isopropylphenyl group, 4- (methanesulfonyl) methylphenyl group, 3-chloro-4- (methanesulfonyl) methylphenyl group, 4- (methanesulfonyl) (2-morpholinoethyl) Aminophenyl group, 4- (methanesulfonyl) (2 Piperidinoethyl) aminophenyl group, 4- (methanesulfonyl) (2-hydroxyethyl) aminophenyl group, 4- (methanesulfonyl) isopropylaminophenyl group, 4- (methanesulfonyl) (2-hydroxy-3- (piperidine-1) -Yl) propyl) aminophenyl group, 4- (methanesulfonyl) (2- (pyrrolidin-1-yl) ethyl) aminophenyl group, 4- (propanesulfonyl) carbamoylphenyl group, 4- (tert-butanesulfonyl) carbamoyl 28. The compound according to item 27, which is a phenyl group or a 4- (ethanesulfonyl) carbamoylphenyl group.
(Item 29)
L 1 Is a bond,
R a Is a cycloheptyl group, a pyridinyl group, a pyrimidinyl group or a phenyl group,
R b Is a phenyl group,
L 2 Is a bond,
R c 4. The compound according to item 3, wherein is a cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, cycloalkylalkyl group, heterocycloalkyl group-alkyl group, aralkyl group or heteroaralkyl group.
(Item 30)
L 1 Is a bond,
R a Is a cycloheptyl group or a phenyl group,
R b Is a phenyl group,
L 2 Is a bond,
R c 4. The compound according to item 3, wherein is a tetrazolyl group, morpholino group or piperazinyl group, and may be optionally substituted.
(Item 31)
R a 31. The compound according to item 30, wherein is a phenyl group having at least one substituent at the para position.
(Item 32)
R a 32. The compound according to item 31, wherein is a p-methoxyphenyl group or a p-hydroxyphenyl group.
(Item 33)
L 1 Is a bond,
R a Is a cycloheptyl group, pyridinyl group, pyrimidinyl group or phenyl group substituted with an alkoxyl group,
R b Is a phenyl group,
L 2 -O-, -S-, -SO 2 -, -CO-, -CO-O-, -NR x -, -NR x -CO-, -NR x -SO 2 -, -NR x -CO-O-, -NR x -CO-NR y -Or-NR x -CO-CO-O-,
And R x Is hydrogen, an alkyl group, -CO-alkyl group, -SO 2 -Alkyl group or -SO 2 An aryl group,
R c 4. The compound according to item 3, wherein is hydrogen, an alkyl group or an aryl group.
(Item 34)
L 1 Is a bond and R a Is a cycloheptyl group or a phenyl group,
R b Is a phenyl group,
L 2 -CO-O-, -NR x -, -NR x -SO 2 -, -NR x -CO-O- or -NR x -CO-NR y -And
And R x Is hydrogen, an alkyl group, -CO-alkyl group, -SO 2 -Alkyl group or -SO 2 An aryl group,
R c 4. The compound according to item 3, wherein is hydrogen, an alkyl group or an aryl group.
(Item 35)
R x -SO 2 -An alkyl group,
R c 35. The compound according to item 34, wherein is an alkyl group.
(Item 36)
R a 35. The compound according to item 34, wherein is a phenyl group having at least one substituent at the para position.
(Item 37)
R a 38. The compound according to item 36, wherein is a p-methoxyphenyl group or a p-hydroxyphenyl group.
(Item 38)
L 1 Is an alkyl group,
R a Is a phenyl group,
R b Is a phenyl group,
L 2 -CO-O-, -NR x -, -NR x -SO 2 -, -NR x -CO-O- or -NR x -CO-NR y Because
And R x And R y Each independently represents hydrogen, an alkyl group, -CO-alkyl group, -SO 2 -Alkyl group or -SO 2 An aryl group,
R c 4. The compound according to item 3, wherein is hydrogen, an alkyl group or an aryl group.
(Item 39)
L 1 40. The compound according to Item 38, wherein is a methyl group substituted with a phenyl group.
(Item 40)
L 1 Is a methyl group,
R x -SO 2 -An alkyl group,
R c 40. The compound of item 38, wherein is an optionally substituted alkyl group.
(Item 41)
R b Is a phenyl group,
L 2 Is a bond or -NR x -SO 2 −
R x Is hydrogen or -SO 2 -An alkyl group,
R c 2. The compound according to item 1, wherein is hydrogen, an alkyl group, a heterocycloalkyl group, a heteroaryl group, a (heterocycloalkyl) alkyl group or a heteroaralkyl group.
(Item 42)
R x -SO 2 -An alkyl group,
R c 42. The compound according to item 41, wherein is an alkyl group.
(Item 43)
R a A compound according to item 1, wherein is a cyclohexyl group optionally substituted with 1 to 3 substituents.
(Item 44)
44. The compound according to item 43, wherein any of the substituents is selected from the group consisting of an alkoxycarbonyl group, a hydroxyalkyl group, a hydroxycarbonyl group, an alkoxycarbonylamino group, and a hydroxycarbonylamino group.
(Item 45)
R a 45. A compound according to item 44, wherein is an ethoxycarbonyl group, a hydroxymethyl group, a hydroxycarbonyl group or a tert-butoxycarbonylamino group.
(Item 46)
R 3 Is 4- (4-methylpiperazin-1-yl) phenyl) group, 4- (piperazin-1-yl) phenyl group, 4-aminophenyl group, 4-benzoic acid group, 4-morpholinophenyl group, 4-N , N-dimethylsulfonylphenyl group or 4- (methanesulfonamido) phenyl group.
(Item 47)
The compound is
N- (4- (1- (3-methoxyphenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenyl) -N- (methylsulfonyl) methanesulfonamide, N- (4- ( 1- (4-methoxyphenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenyl) -N- (methylsulfonyl) methanesulfonamide, N- (4- (1- (4-methoxy Phenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenyl) cyclopropanesulfonamide, 1- (4-methoxyphenyl) -N- (3- (4-methylpiperazin-1-yl) Phenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, 2-hydroxy-5- (1- (4-methoxyphenyl) -1H-pyrazolo [3,4-d Pyrimidin-6-ylamino) benzaldehyde, ethyl 2- (4- (1- (4-methoxyphenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenylamino) -2-oxoacetate, N -(2,3,5,6,8,9,11,12,14,15-decahydrobenzo [b]-[1,4,7,10,13,16] hexaoxacyclooctadecine-18- Yl) -1- (4-methoxyphenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, 1- (4-methoxyphenyl) -N- (2,3,5,6,8, 9,11,12-octahydrobenzo [b]-[1,4,7,10,13] pentaoxacyclopentadecin-15-yl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine , N- (4- (1 (4-Methoxyphenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenyl) -1- (methylsulfonyl) methanesulfonamide, 3,3,3-trifluoro-N- (4- (1- (4-Methoxyphenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenyl) propane-1-sulfonamide, 1- (4-methoxyphenyl) -N- (4-morpholino Phenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, N- (4- (1H-1,2,4-triazol-1-yl) phenyl) -1- (4-methoxyphenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, 2-methoxy-4- (1- (4-methoxyphenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-yla Mino) phenol, N- (3,4-dimethoxyphenyl) -1- (4-methoxyphenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, 1- (3- (1- (4 -Methoxyphenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenyl) ethanol, N 1 -(1- (4-methoxyphenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-yl) benzene-1,4-diamine, N- (4- (1- (4-methoxyphenyl)- 1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenyl) methanesulfonamide, 4- (1- (4-methoxyphenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) Phenol, 1- (4-methoxyphenyl) -N- (3,4,5-trimethoxyphenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, 1- (4-methoxyphenyl)- N- (4- (4- (methylsulfonyl) piperazin-1-yl) phenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, methyl-3- (4- (1- (4- Methoxypheni ) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenylamino) -3-oxopropanoate, 2-methoxy-N- (4- (1- (4-methoxyphenyl) -1H- Pyrazolo [3,4-d] pyrimidin-6-ylamino) phenyl) acetamide, N- (3,4-dihydro-2H-benzo [b] [1,4] dioxepin-7-yl) -1- (4- Methoxyphenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, 2-ethoxy-5- (1- (4-methoxyphenyl) -1H-pyrazolo [3,4-d] pyrimidine-6- Ylamino) phenol, 2- (4- (1- (4-methoxyphenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenyl) ethanol, N- (4- (1- (4- Meto Ciphenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenyl) acetamide, 2- (2-methoxyethoxy) -N- (4- (1- (4-methoxyphenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenyl) acetamide, diethyl 4- (1- (4-methoxyphenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) benzylphosphonate, 1 -(3-methoxyphenyl) -N- (4- (4- (methylsulfonyl) piperazin-1-yl) phenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, dimethyl-4- ( 1- (4-methoxyphenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenyl phosphoramidate, N 1 -(1- (3-methoxyphenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-yl) benzene-1,4-diamine, 1- (4-methoxyphenyl) -N- (4- ( 4-methylpiperazin-1-yl) phenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, N- (3-methoxyphenyl) -1- (4-methoxyphenyl) -1H-pyrazolo [ 3,4-d] pyrimidin-6-amine, 3- (1- (4-methoxyphenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenol, 1- (4-methoxyphenyl) -N- (4- (piperidin-1-yl) phenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, N 1 -Bis (4-methoxyphenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, methyl-4- (1- (4-methoxyphenyl) -1H-pyrazolo [3,4-d] pyrimidine -6-ylamino) phenylcarbamate, 2- (4- (1- (4-methoxyphenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenylamino) -2-oxoethyl acetate, N -(2,3-dihydrobenzo [b] [1,4] dioxin-6-yl) -1- (4-methoxyphenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, 2- Methoxy-5- (1- (4-methoxyphenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenol, 1- (4-methoxyphenyl) -N- (4- (methyl) Thio) phenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, 4- (1- (4-methoxyphenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino)- 2-methylphenol, 2-methoxy-4- (1- (3-methoxyphenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenol, N- (3,4-dimethoxyphenyl)- 1- (3-methoxyphenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, 2- (2-methoxyethoxy) -N- (4- (1- (4-methoxyphenyl) -1H -Pyrazolo [3,4-d] pyrimidin-6-ylamino) phenyl) acetamide, (E) -N '-(4- (1- (4-methoxyphenyl) -1H-pyrazolo [3,4-d] pyrimidine − -Ylamino) phenyl) -N, N-dimethylformimidamide, 2-methoxy-5- (1- (3-methoxyphenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenol, N -(2,2-dimethylbenzo [d] [1,3] dioxol-5-yl) -1- (4-methoxyphenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, methyl 2 -Hydroxy-5- (1- (4-methoxyphenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) benzoate, 1- (4-methoxyphenyl) -N- (4- (methyl Sulfonyl) phenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, 3- (1- (3-methoxyphenyl) -1H-pyrazolo [3,4-d] pyrimidine-6-i Amino) phenol, 1- (3-methoxyphenyl) -N- (2,3,5,6,8,9,11,12-octahydrobenzo [b]-[1,4,7,10,13] Pentaoxacyclopentadecin-15-yl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, N- (benzo [d] [1,3] dioxol-5-yl) -1- (3 -Methoxyphenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, N- (4- (1- (4-methoxyphenyl) -1H-pyrazolo [3,4-d] pyrimidine-6- Ylamino) phenyl) -N-methylmethanesulfonamide, 4-methoxy-N- (4- (1- (4-methoxyphenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenyl) benzamide , N- (2, 4-Dimethoxyphenyl) -1- (3-methoxyphenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, 1- (4-methoxyphenyl) -N- (naphthalen-1-yl)- 1H-pyrazolo [3,4-d] pyrimidin-6-amine, N- (4- (1-cycloheptyl-1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenyl) -N- (methyl Sulfonyl) methanesulfonamide, N- (4- (1H-tetrazol-5-yl) phenyl) -1-cycloheptyl-1H-pyrazolo [3,4-d] pyrimidin-6-amine, N, N-dimethyl- 4- (1-cycloheptyl-1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenylsulfamide, N 1 -(1-cycloheptyl-1H-pyrazolo [3,4-d] pyrimidin-6-yl) benzene-1,4-diamine, 3-chloro-N- (4- (1-cycloheptyl-1H-pyrazolo [ 3,4-d] pyrimidin-6-ylamino) phenyl) propane-1-sulfonamide, 3-chloro-N- (4- (1-cycloheptyl-1H-pyrazolo [3,4-d] pyrimidine-6 Ylamino) phenyl) -propyl-1,3-sultam, 1-cycloheptyl-N- (4- (4- (methylsulfonyl) piperazin-1-yl) phenyl) -1H-pyrazolo [3,4-d] pyrimidine -6-amine, 4- (1-cycloheptyl-1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) benzoic acid, 1-cycloheptyl-N- (4-morpholinophenyl) 1H-pyrazolo [3,4-d] pyrimidin-6-amine, 3-chloro-N- (3-chloropropylsulfonyl) -N- (4- (1-cycloheptyl-1H-pyrazolo [3,4-d ] Pyrimidin-6-ylamino) phenyl) propane-1-sulfonamide, (4- (1-cycloheptyl-1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenyl) (morpholino) methanone, N 1 -(1-cycloheptyl-1H-pyrazolo [3,4-d] pyrimidin-6-yl) benzene-1,3-diamine, 1- (4- (1-cycloheptyl-1H-pyrazolo [3,4 d] pyrimidin-6-ylamino) phenyl) guanidine, N- (4- (1-cycloheptyl-1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenyl) methanesulfonamide, dimethyl-4- ( 4- (1-cycloheptyl-1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenyl) piperazin-1-ylphosphonate, (4- (1-cycloheptyl-1H-pyrazolo [3,4 d] pyrimidin-6-ylamino) phenyl) (4-ethylpiperazin-1-yl) methanone, 1-cycloheptyl-N- (4-thiomorpholinophenyl) 1H-pyrazolo [3,4-d] pyrimidin-6-amine, dimethyl-4- (1-cycloheptyl-1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenyl phosphoramidate, 1- Cycloheptyl-N- (4- (piperazin-1-yl) phenyl) -1H-pyrazolo [3,4-d] pyrimidine-
6-amine, 1-cycloheptyl-N- (4- (1-methyl-1H-tetrazol-5-yl)
Phenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, 2- (4- (1-cycloheptyl-1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenyl) ethanol, 1-allyl-3- (4- (1-cycloheptyl-1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenyl) urea, N- (4- (1-cycloheptyl-1H-pyrazolo [ 3,4-d] pyrimidin-6-ylamino) phenyl) acetamide, 1- (4- (1-cycloheptyl-1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenyl) -3-ethylurea 1- (4- (1-cycloheptyl-1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenyl) -3-propylurea, 1-cycloheptyl-N- (4- 4-methylpiperazin-1-yl) phenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, 1-cycloheptyl-N- (4- (2-methyl-2H-tetrazol-5-yl) ) Phenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, N- (4- (2- (2-chloroethyl) -2H-tetrazol-5-yl) phenyl) -1-cycloheptyl- 1H-pyrazolo [3,4-d] pyrimidin-6-amine, N- (4- (1-cycloheptyl-1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenyl) thiophene-2-sulfone Amides, 4- (1-cycloheptyl-1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) benzonitrile, N- (3- (1-cycloheptyl-1H-pyrazolo [3 4-d] pyrimidin-6-ylamino) phenyl) -N- (methylsulfonyl) methanesulfonamide, 1-cycloheptyl-N- (4- (piperidin-1-yl) phenyl) -1H-pyrazolo [3,4 -D] pyrimidin-6-amine, N- (4- (1-cycloheptyl-1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenyl) -1- (methylsulfonyl) -N- (methyl Sulfonylmethylsulfonyl) methanesulfonamide, 1-cycloheptyl-N- (4- (2-morpholinoethoxy) phenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, N- (4- (1H -Pyrazol-1-yl) phenyl) -1-cycloheptyl-1H-pyrazolo [3,4-d] pyrimidin-6-amine, N- (4- (1-cyclo Heptyl-1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenyl) -N- (phenylsulfonyl) benzenesulfonamide, N- (1-cycloheptyl-1H-pyrazolo [3,4-d] pyrimidine -6-yl) -1,1,1-trifluoro-N- (4- (1,1,1-trifluoro-N- (trifluoromethylsulfonyl) methylsulfonamido) phenyl) methane-sulfonamide, N -(Benzo [d] [1,3] dioxol-5-yl) -1-cycloheptyl-1H-pyrazolo [3,4-d] pyrimidin-6-amine, 2- (4- (4- (1- Cycloheptyl-1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenyl) piperazin-1-yl) ethanol, 1-cycloheptyl-N-phenyl-1H- Lazolo [3,4-d] pyrimidin-6-amine, 1-cycloheptyl-N- (4- (2-vinyl-2H-tetrazol-5-yl) phenyl) -1H-pyrazolo [3,4-d] Pyrimidin-6-amine, ethyl 4- (1-cycloheptyl-1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) benzoate, tert-butyl 4- (4- (1-cycloheptyl-1H- Pyrazolo [3,4-d] pyrimidin-6-ylamino) phenyl) piperazine-1-carboxylate, N- (4- (1- (4-methoxy-2-methylphenyl) -1H-pyrazolo [3,4 d] pyrimidin-6-ylamino) phenyl) -N- (methylsulfonyl) methanesulfonamide, 1- (4-methoxy-2-methylphenyl) -N- (4- (4- (methyl) Sulfonyl) piperazin-1-yl) phenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, 1- (4-methoxy-2-methylphenyl) -N- (4- (4-methylpiperazine) -1-yl) phenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, N- (4- (1- (4-methoxy-2-methylphenyl) -1H-pyrazolo [3,4] -D] pyrimidin-6-ylamino) phenyl) methanesulfonamide, 1- (4-methoxy-2-methylphenyl) -N- (4-methoxyphenyl) -1H-pyrazolo [3,4-d] pyrimidine-6 -Amine, 1- (4-methoxy-2-methylphenyl) -N- (4- (trifluoromethoxy) phenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, 1- (4- Me Toxi-2-methylphenyl) -N- (4- (methylthio) phenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, 2-methoxy-5- (1- (4-methoxy-2) -Methylphenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenol, 3- (6- (4-aminophenylamino) -1H-pyrazolo [3,4-d] pyrimidine-1- Yl) phenol, 4- (6- (4-aminophenylamino) -1H-pyrazolo [3,4-d] pyrimidin-1-yl) phenol, 4- (6- (4-morpholinophenylamino) -1H- Pyrazolo [3,4-d] pyrimidin-1-yl) phenol, 5- (1- (3-hydroxyphenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) -2-methoxy Phenol, 5- (1- (4-hydroxyphenyl) -1H- pyrazolo [3,4-d] pyrimidin-6-ylamino) -2-methoxyphenol, N 1 -(1- (4-Iodophenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-yl) benzene-1,4-diamine, 4- (4- (6- (4-aminophenylamino) -1H-pyrazolo [3,4-d] pyrimidin-1-yl) phenyl) but-3-yn-1-ol, 4- (4- (6- (3,4-dimethoxyphenylamino) -1H-pyrazolo [3,4-d] pyrimidin-1-yl) phenyl) but-3-yn-1-ol, N- (3,4-dimethoxyphenyl) -1- (4-iodophenyl) -1H-pyrazolo [3 , 4-d] pyrimidin-6-amine, 5- (1- (4-iodophenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) -2-methoxyphenol, 1- (4- Ethylphenyl) -N- (4- (piperidi -1-yl) phenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, 1- (4-iodophenyl) -N- (4- (piperidin-1-yl) phenyl) -1H- Pyrazolo [3,4-d] pyrimidin-6-amine, 1-benzyl-N- (4- (piperidin-1-yl) phenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, 1 -(3-methoxybenzyl) -N- (4- (piperazin-1-yl) phenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, 1- (3,4-dimethoxybenzyl)- N- (4- (piperazin-1-yl) phenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, tert-butyl 4- (4- (1- (3,5-dimethoxybenzyl) -1H-pyrazolo [3,4 ] Pyrimidin-6-ylamino) phenyl) piperazine-1-carboxylate, 1- (3,5-dimethoxybenzyl) -N- (4- (piperazin-1-yl) phenyl) -1H-pyrazolo [3,4 d] pyrimidin-6-amine, tert-butyl 4- (4- (3-bromo-1- (3,4-dimethoxybenzyl) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenyl) Piperazine-1-carboxylate, tert-butyl 4- (4- (1- (3,4-dimethoxybenzyl) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenyl) piperazine-1-carboxy 1- (4-methoxybenzyl) -N- (4- (piperazin-1-yl) phenyl) -1H-pyrazolo [3,4-d] pyrimidine-6 -Amine, tert-butyl 4- (4- (1- (4-methoxybenzyl) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenyl) piperazine-1-carboxylate, 1- (2 , 3-Dihydro-1H-inden-2-yl) -N- (4-morpholinophenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, ethyl 2- (4- (1-cycloheptyl) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenyl) acetate, 1-cycloheptyl-N- (4-((4-methylpiperazin-1-yl) methyl) phenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, 2- (4- (1-cycloheptyl-1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenyl) acetic acid, 2- 4- (1-cycloheptyl-1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenyl) -1- (4-ethylpiperazin-1-yl) ethanone, 2- (4- (1-cyclo Heptyl-1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenyl) -N-methylacetamide, 2- (4- (1-cycloheptyl-1H-pyrazolo [3,4-d] pyrimidine-6 -Ylamino) phenyl) -N-isopropylacetamide, ethyl 2- (4- (1-cycloheptyl-1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenyl) -2-methylpropanoate, 2 -(4- (1-Cycloheptyl-1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenyl) -2-methylpropanoic acid, ethyl 2- (2 Chloro-4- (1-cycloheptyl-1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenyl) acetate, 2- (2-chloro-4- (1-cycloheptyl-1H-pyrazolo [3 , 4d] pyrimidin-6-ylamino) phenyl) acetic acid, 2- (4- (1-cycloheptyl-1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenyl) -2-methyl-1- ( 4-methylpiperazin-1-yl) propan-1-one, 1-cycloheptyl-N- (4- (methylsulfonylmethyl) phenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, N -(3-Chloro-4- (methylsulfonylmethyl) phenyl) -1-cycloheptyl-1H-pyrazolo [3,4-d] pyrimidin-6-amine, N- (4- (1-Si Chloheptyl-1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenyl) -N- (2-morpholinoethyl) methanesulfonamide, N- (4- (1-cycloheptyl-1H-pyrazolo [3 4-d] pyrimidin-6-ylamino) phenyl) -N- (2- (piperidin-1-yl) ethyl) methanesulfonamide, N- (4- (1-cycloheptyl-1H-pyrazolo [3,4 d] pyrimidin-6-ylamino) phenyl) -N- (2-hydroxyethyl) methanesulfonamide, N- (4- (1-cycloheptyl-1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) Phenyl) -N-isopropylmethanesulfonamide, N- (4- (1-cycloheptyl-1H-pyrazolo [3,4-d] pyrimidin-6-yla ) Phenyl) -N- (2-hydroxy-3- (piperidin-1-yl) propyl) methanesulfonamide, N- (4- (1-cycloheptyl-1H-pyrazolo [3,4-d] pyrimidine- 6-ylamino) phenyl) -N- (2- (pyrrolidin-1-yl) ethyl) methanesulfonamide, N- (4- (1- (4-hydroxy-2,3-dihydro-1H-indene-1-) Yl) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenyl) -N- (methylsulfonyl) methanesulfonamide, (S) -N- (4- (1- (2,3-dihydro) -1H-inden-1-yl) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenyl) -N- (ethylsulfonyl) ethanesulfonamide, 1- (6- (4- (4- Chill piperazin-1-yl) phenylamino) -1H- pyrazolo [3,4-d] Pirimi
Gin-1-yl)
-2,3-dihydro-1H-inden-4-ol, 1- (6- (4- (N- (methylsulfonyl) methylsulfonamido) phenylamino) -1H-pyrazolo [3,4-d] pyrimidine- 1-yl) -2,3-dihydro-1H-inden-4-ylbenzoate, 1- (6- (4- (N- (methylsulfonyl) methylsulfonamido) phenylamino) -1H-pyrazolo [3 4-d] pyrimidin-1-yl) -2,3-dihydro-1H-inden-4-yl dihydrogen phosphate, (S) -1-chloro-N- (chloromethylsulfonyl) -N- (4- ( 1- (2,3-dihydro-1H-inden-1-yl) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenyl) methanesulfonamide, N- (4- (1- (6 , 7-G Dro-5H-indeno [5,6-d] [1,3] dioxol-5-yl) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenyl) -N- (methylsulfonyl) methane Sulfonamide, N- (1- (6- (4- (N- (methylsulfonyl) methylsulfonamido) phenylamino) -1H-pyrazolo [3,4-d] pyrimidin-1-yl) -2,3- Dihydro-1H-inden-5-yl) acetamide, N- (4- (1- (4-hydroxy-2,3-dihydro-1H-inden-1-yl) -1H-pyrazolo [3,4-d] Pyrimidin-6-ylamino) phenyl) methanesulfonamide, 1- (6- (4- (N- (methylsulfonyl) methylsulfonamido) phenylamino) -1H-pyrazolo [3,4-d] pyri Gin-1-yl) -2,3-dihydro-1H-inden-5-ylbenzoate, (S, Z) -4- (1- (2,3-dihydro-1H-inden-1-yl)- 1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) -N′-hydroxybenzimidoamide, 1- (6- (4- (4-methylpiperazin-1-yl) phenylamino) -1H-pyrazolo [3,4-d] pyrimidin-1-yl) -2,3-dihydro-1H-inden-4-ylbenzoate, 1- (6- (4-aminophenylamino) -1H-pyrazolo [3,4 -D] pyrimidin-1-yl) -2,3-dihydro-1H-inden-4-ol, 1- (6- (4-aminophenylamino) -1H-pyrazolo [3,4-d] pyrimidine-1 -Yl) -2,3-dihydro-1H Inden-4-ylbenzoate, di-tert-butyl 1- (6- (4- (N- (methylsulfonyl) methylsulfonamido) phenylamino) -1H-pyrazolo [3,4-d] pyrimidine-1- Yl) -2,3-dihydro-1H-inden-4-yl phosphate, (S) -4- (1- (2,3-dihydro-1H-inden-1-yl) -1H-pyrazolo [3,4 -D] pyrimidin-6-ylamino) -N- (methylsulfonyl) benzamide, N- (4- (1- (5-((2-methoxyethoxy) methoxy) -2,3-dihydro-1H-indene-1 -Yl) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenyl) -N- (methylsulfonyl) methanesulfonamide, N- (1- (6- (4-aminophenylamino) ) -1H-pyrazolo [3,4-d] pyrimidin-1-yl) -2,3-dihydro-1H-inden-5-yl) acetamide, (S) -4- (1- (2,3-dihydro) -1H-inden-1-yl) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) benzonitrile, (S) -N- (4- (1H-tetrazol-5-yl) phenyl)- 1- (2,3-dihydro-1H-inden-1-yl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, N1- (1- (5-methoxy-2,3-dihydro- 1H-inden-1-yl) -1H-pyrazolo [3,4-d] pyrimidin-6-yl) benzene-1,4-diamine, N- (4- (1- (5-methoxy-2,3- Dihydro-1H-inden-1-yl) -1H-pyrazolo [3 4-d] pyrimidin-6-ylamino) phenyl) -N- (methylsulfonyl) methanesulfonamide, (S) -1- (2,3-dihydro-1H-inden-1-yl) -N- (4- Nitrophenethyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, (S) -N- (4-aminophenethyl) -1- (2,3-dihydro-1H-inden-1-yl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, (S) -N- (4- (2- (1- (2,3-dihydro-1H-inden-1-yl) -1H- Pyrazolo [3,4-d] pyrimidin-6-ylamino) ethyl) phenyl) -N- (methylsulfonyl) methanesulfonamide, N- (4- (1- (1H-indol-4-yl) -1H-pyrazolo) [3,4-d] pyrimidine 6-ylamino) phenyl) -N- (methylsulfonyl) methanesulfonamide, N- (4- (1- (1H-indol-6-yl) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) ) Phenyl) -N- (methylsulfonyl) methanesulfonamide, N- (4- (1- (1H-indol-5-yl) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenyl) -N- (methylsulfonyl) methanesulfonamide, N- (4- (1- (benzo [d] [1,3] dioxol-5-yl) -1H-pyrazolo [3,4-d] pyrimidine-6 Ylamino) phenyl) -N- (methylsulfonyl) methanesulfonamide, 1- (1H-indol-4-yl) -N- (4- (4-methylpiperazin-1-yl) phenyl ) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, N- (4- (1- (1-methyl-1H-indol-5-yl) -1H-pyrazolo [3,4-d]) Pyrimidin-6-ylamino) phenyl) -N- (methylsulfonyl) methanesulfonamide, 1- (7-methyl-1H-indol-4-yl) -N- (4- (4-methylpiperazin-1-yl) Phenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, tert-butyl 7-methyl-4- (6- (4- (4-methylpiperazin-1-yl) phenylamino) -1H- Pyrazolo [3,4-d] pyrimidin-1-yl) -1H-indole-1-carboxylate, tert-butyl 4- (6- (4- (4-methylpiperazin-1-yl) phenylamino) -1H -Pi Zolo [3,4-d] pyrimidin-1-yl) -1H-indole-1-carboxylate, N- (4-morpholinophenyl) -1- (naphthalen-1-ylmethyl) -1H-pyrazolo [3,4 -D] pyrimidin-6-amine, 1-butyl-N- (4- (piperidin-1-yl) phenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, 1-isopropyl-N- (4- (Piperidin-1-yl) phenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, 1- (cyclopentylmethyl) -N- (4- (piperidin-1-yl) phenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, (S) -N- (4-morpholinophenyl) -1- (1-phenylethyl) -1H-pyrazolo [3,4-d] pyrimidine − -Amine, 1-((6-fluoro-4H-benzo [d] [1,3] dioxin-8-yl) methyl) -N- (4-morpholinophenyl) -1H-pyrazolo [3,4-d] Pyrimidin-6-amine, 1- (furan-2-ylmethyl) -N- (4- (piperazin-1-yl) phenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, ethyl 2- (6- (4- (piperidin-1-yl) phenylamino) -1H-pyrazolo [3,4-d] pyrimidin-1-yl) acetate, N- (4-morpholinophenyl) -1- (pyridine-2 -Ylmethyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, 1-methyl-N- (4- (piperidin-1-yl) phenyl) -1H-pyrazolo [3,4-d] pyrimidine -6-amine, N- (4-morpholinophenyl) -1- (1,2,3,4-tetrahydronaphthalen-1-yl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, 1- (1-benzylpiperidine- 4-yl) -N- (4-morpholinophenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine or 1-((4-methoxy-3,5-dimethylpyridin-2-yl) 2. The compound according to item 1, which is methyl) -N- (4-morpholinophenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine.
(Item 48)
The compound is
N- (4- (1H-tetrazol-5-yl) phenyl) -1-cycloheptyl-1H-pyrazolo [3,4-d] pyrimidin-6-amine, N- (4- (1H-tetrazol-5- Yl) phenyl) -1- (biphenyl-2-yl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, N- (4- (1H-tetrazol-5-yl) phenyl) -1- (3-methoxyphenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, N- (4- (1H-tetrazol-5-yl) phenyl) -1- (4-methoxyphenyl) -1H -Pyrazolo [3,4-d] pyrimidin-6-amine, 1-cycloheptyl-N- (4-morpholinophenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, 1- (biphenyl- 2-yl) N- (4-morpholinophenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, N- (4-morpholinophenyl) -1- (phenanthren-4-yl) -1H-pyrazolo [3 4-d] pyrimidin-6-amine, 1- (3-methoxyphenyl) -N- (4-morpholinophenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, 1- (4-methoxy Phenyl) -N- (4-morpholinophenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, 1-cycloheptyl-N- (4- (piperazin-1-yl) phenyl) -1H- Pyrazolo [3,4-d] pyrimidin-6-amine, 1- (biphenyl-2-yl) -N- (4- (piperazin-1-yl) phenyl) -1H-pyrazolo [3,4-d] pyrimidine − -Amine, 1- (3-methoxyphenyl) -N- (4- (piperazin-1-yl) phenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, 1- (4-methoxyphenyl) ) -N- (4- (piperazin-1-yl) phenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, 4- (1-cycloheptyl-1H-pyrazolo [3,4-d ] Pyrimidin-6-ylamino) benzoic acid, 4- (1- (biphenyl-2-yl) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) benzoic acid, 4- (1- (3- Methoxyphenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) benzoic acid, 4- (1- (4-methoxyphenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino ) Benzoic acid, N 1 -(1-cycloheptyl-1H-pyrazolo [3,4-d] pyrimidin-6-yl) benzene-1,4-diamine, N 1 -(1- (biphenyl-2-yl) -1H-pyrazolo [3,4-d] pyrimidin-6-yl) benzene-1,4-diamine, N 1 -(1- (3-methoxyphenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-yl) benzene-1,4-diamine, N 1 -(1- (4-methoxyphenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-yl) benzene-1,4-diamine, N- (4- (1-cycloheptyl-1H-pyrazolo [ 3,4-d] pyrimidin-6-ylamino) phenyl) -N- (methylsulfonyl) methanesulfonamide, N- (4- (1- (biphenyl-2-yl) -1H-pyrazolo [3,4-d ] Pyrimidin-6-ylamino) phenyl) -N- (methylsulfonyl) methanesulfonamide, N- (4- (1- (3-methoxyphenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) ) Phenyl) -N- (methylsulfonyl) methanesulfonamide, N- (4- (1- (4-methoxyphenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) Phenyl) -N- (methylsulfonyl) methanesulfonamide, N- (4- (1-cycloheptyl-1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenyl) methanesulfonamide, N- (4 -(1- (biphenyl-2-yl) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenyl) methanesulfonamide, N- (4- (1- (phenanthren-4-yl)- 1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenyl) methanesulfonamide, N- (4- (1- (3-methoxyphenyl) -1H-pyrazolo [3,4-d] pyrimidine-6 -Ylamino) phenyl) methanesulfonamide, N- (4- (1- (4-methoxyphenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-yla B) phenyl) methanesulfonamide, 1-cycloheptyl-N- (4- (4-methylpiperazin-1-yl) phenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, 1- ( Biphenyl-2-yl) -N- (4- (4-methylpiperazin-1-yl) phenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, 1- (3-methoxyphenyl)- N- (4- (4-methylpiperazin-1-yl) phenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, 1- (4-methoxyphenyl) -N- (4- (4 -Methylpiperazin-1-yl) phenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, 5- (1-cycloheptyl-1H-pyrazolo [3,4-d] pyrimidin-6-ylamino ) -2- Methoxyphenol, 5- (1- (biphenyl-2-yl) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) -2-methoxyphenol, 2-methoxy-5- (1- (3- Methoxyphenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenol, 4- (6- (4- (N- (methylsulfonyl) methylsulfonamido) phenylamino) -1H-pyrazolo [3 , 4-d] pyrimidin-1-yl) phenyl dihydrogen phosphate 4-methoxy-N1- (1- (4-methoxyphenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-yl) benzene-1 , 3-diamine 4- (6- (4- (N- (methylsulfonyl) methylsulfonamido) phenylamino) -1H-pyrazolo [3,4-d] pyrimidine-1 Yl) phenyl acetate 4- (6- (4- (N- (methylsulfonyl) methylsulfonamido) phenylamino) -1H-pyrazolo [3,4-d] pyrimidin-1-yl) phenylsulfamate N- ( 4- (1- (4-hydroxyphenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenyl) -N- (methylsulfonyl) methanesulfonamide, 2-methoxy-5- (1- (4-Methoxyphenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenol, 1- (cyclopentylmethyl) -N- (4- (piperidin-1-yl) phenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, (S) -N- (4-morpholinophenyl) -1- (1-phenylethyl) -1H-pyrazolo 3,4-d] pyrimidin-6-amine, 1-((6-fluoro-4H-benzo [d] [1,3] dioxin-8-yl) methyl) -N- (4-morpholinophenyl) -1H -Pyrazolo [3,4-d] pyrimidin-6-amine, 1- (furan-2-ylmethyl) -N- (4- (piperazin-1-yl) phenyl) -1H-pyrazolo [3,4-d] Pyrimidin-6-amine, N- (4-morpholinophenyl) -1- (pyridin-2-ylmethyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, 1- (1-benzylpiperidine-4 -Yl) -N- (4-morpholinophenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, 1-((4-methoxy-3,5-dimethylpyridin-2-yl) methyl) -N- (4-morpholino Phenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, N- (5- (1-cycloheptyl-1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) pyridine-2- Yl) -N- (methylsulfonyl) methanesulfonamide, N- (5- (1-cycloheptyl-1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) pyridin-2-yl) methanesulfonamide, N- (5- (1-cycloheptyl-1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) pyridin-2-yl) -N- (2-hydroxyethyl) methanesulfonamide, N- (4 -(6- (6- (N- (methylsulfonyl) methylsulfonamido) pyridin-3-ylamino) -1H-pyrazolo [3,4-d] pyrimidin-1-yl) phenyl 2- (Pyrrolidin-1-yl) acetamide, N- (4- (6- (6- (methylsulfonamido) pyridin-3-ylamino) -1H-pyrazolo [3,4-d] pyrimidin-1-yl ) Phenyl) -2- (pyrrolidin-1-yl) acetamide, N- (5- (1-cycloheptyl-1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) pyridin-2-yl) -N -(2-morpholinoethyl) methanesulfonamide, N- (5- (1-cycloheptyl-1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) pyridin-2-yl) -N- (2, 3-dihydroxypropyl) methanesulfonamide, N- (4- (6- (6- (N- (2,3-dihydroxypropyl) methylsulfonamido) pyridin-3-ylamino) -1H Pyrazolo [3,4-d] pyrimidin-1-yl) phenyl) -2- (pyrrolidin-1-yl) acetamide, tert-butyl 4- (6- (6- (N- (2,3-dihydroxypropyl)) Methylsulfonamido) pyridin-3-ylamino) -1H-pyrazolo [3,4-d] pyrimidin-1-yl) phenylcarbamate, tert-butyl 4- (6- (6- (N- (2-morpholinoethyl)) Methylsulfonamido) pyridin-3-ylamino) -1H-pyrazolo [3,4-d] pyrimidin-1-yl) phenylcarbamate, N- (5- (1-cycloheptyl-1H-pyrazolo [3,4-d ] Pyrimidin-6-ylamino) pyrimidin-2-yl) methanesulfonamide, N- (5- (1-cycloheptyl-1H-pyrazolo [3,4-d]) Pyrimidin-6-ylamino) pyrimidin-2-yl) -N- (2,3-dihydroxypropyl) methanesulfonamide, tert-butyl 4- (6- (2- (N- (2,3-dihydroxypropyl) methyl) Sulfonamido) pyrimidin-5-ylamino) -1H-pyrazolo [3,4-d] pyrimidin-1-yl) phenylcarbamate, N- (5- (1-cycloheptyl-1H-pyrazolo [3,4-d]) Pyrimidin-6-ylamino) pyrimidin-2-yl) -N- (2-morpholinoethyl) methanesulfonamide, N- (4- (6- (2- (N- (2,3-dihydroxypropyl) methylsulfonamide) ) Pyrimidin-5-ylamino) -1H-pyrazolo [3,4-d] pyrimidin-1-yl) phenyl) -2- (pyrrolidin-1-yl) Acetamide, tert-butyl 4- (6- (2- (N- (2-morpholinoethyl) methylsulfonamido) pyrimidin-5-ylamino) -1H-pyrazolo [3,4-d] pyrimidin-1-yl) phenyl Carbamate, tert-butyl 5- (6- (2- (N- (2-morpholinoethyl) methylsulfonamido) pyrimidin-5-ylamino) -1H-pyrazolo [3,4-d] pyrimidin-1-yl) pyridine 2-ylcarbamate, N- (5- (6- (2- (N- (2,3-dihydroxypropyl) methylsulfonamido) pyrimidin-5-ylamino) -1H-pyrazolo [3,4-d] pyrimidine -1-yl) pyridin-2-yl) -2- (pyrrolidin-1-yl) acetamide, N- (5- (6- (6- (N- (2,3-dihydro)) Roxypropyl) methylsulfonamido) pyridin-3-ylamino) -1H-pyrazolo [3,4-d] pyrimidin-1-yl) pyridin-2-yl) -2- (pyrrolidin-1-yl) acetamide, tert- Butyl 5- (6- (6- (N- (2-morpholinoethyl) methylsulfonamido) pyridin-3-ylamino) -1H-pyrazolo [3,4-d] pyrimidin-1-yl) pyridin-2-yl Carbamate, tert-butyl 6- (6- (6- (N- (2-morpholinoethyl) methylsulfonamido) pyri
Gin-3-ylamino) -1H-pyrazolo [3,4-d] pyrimidi
N-1-yl) pyridin-3-ylcarbamate, N- (6- (6- (6- (N- (2,3-dihydroxypropyl) methylsulfonamido) pyridin-3-ylamino) -1H-pyrazolo [ 3,4-d] pyrimidin-1-yl) pyridin-3-yl) -2- (pyrrolidin-1-yl) acetamide, tert-butyl 6- (6- (2- (N- (2,3-dihydroxy) Propyl) methylsulfonamido) pyrimidin-5-ylamino) -1H-pyrazolo [3,4-d] pyrimidin-1-yl) pyridin-3-ylcarbamate, tert-butyl 6- (6- (6- (N-- (2,3-dihydroxypropyl) methylsulfonamido) pyridin-3-ylamino) -1H-pyrazolo [3,4-d] pyrimidin-1-yl) pyridin-3-ylcal Mate, N- (5- (1- (3-hydroxybenzyl) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) pyridin-2-yl) methanesulfonamide, N- (2,3- Dihydroxypropyl) -N- (5- (1- (3-hydroxybenzyl) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) pyridin-2-yl) methanesulfonamide, N- (2, 3-dihydroxypropyl) -N- (5- (1- (2-hydroxypyridin-4-yl) methyl) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) pyridin-2-yl) methane Sulfonamide, N- (5- (1- (3-hydroxybenzyl) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) pyridin-2-yl) -N- (2-mol Linoethyl) methanesulfonamide, N- (2,3-dihydroxypropyl) -N- (4- (1-((2-hydroxypyridin-4-yl) methyl) -1H-pyrazolo [3,4-d] pyrimidine -6-ylamino) phenyl) methanesulfonamide or N- (5- (1-((2-hydroxypyridin-4-yl) methyl) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) 2. The compound according to item 1, which is) pyridin-2-yl) -N- (2-morpholinoethyl) methanesulfonamide.
(Item 49)
49. A pharmaceutical composition comprising the compound according to any one of items 1 to 48 and a pharmacologically acceptable carrier.
(Item 50)
49. A method of treating a subject suffering from a protein kinase mediated disease comprising administering to the subject a pharmacologically effective amount of a compound according to any one of items 1 to 48. .
(Item 51)
49. A method of inhibiting protease kinase in a cell, comprising contacting the cell with a compound according to any one of items 1 to 48.
(Item 52)
52. The method of item 51, wherein the protease kinase is one or more protease kinases involved in cell mitosis.
(Item 53)
53. The method of item 52, wherein the protease kinase is Aurora kinase or cyclin-dependent kinase.
(Item 54)
49. A method of treating a tumor or cancer in a subject comprising administering to a subject in need of such treatment a compound according to any one of items 1 to 48.
(Item 55)
The tumor or cancer is bone cancer, brain and CNS tumor, breast cancer, breast cancer, colorectal cancer, endocrine cancer, gastrointestinal cancer, genitourinary cancer, gynecological cancer, head and neck cancer, leukemia, lung cancer, lymphoma 55. The method of item 54, wherein the disease is eye cancer, skin cancer, soft tissue sarcoma, urinary cancer, and other types or related disorders.
The present invention relates to a compound of formula (I),
Claims (31)
(式中、R1は水素又はハロ基であり、
R2は−L1−Raであり、
L1は結合又はアルキル基であり、
Raはシクロヘキシル基、シクロヘプチル基、ピペリジニル基、ピロリジニル基、フリル基、チエニル基、モルホリニル基、ピリジニル基又はピリミジニル基であり、各々1〜3個の置換基で任意に置換されてもよいか、又は、
Raは置換フェニル基であり、
R3は−Rb−L2−Rcであり、
Rbはアリール基、ヘテロアリール基、シクロアルキル基又はヘテロシクロアルキル基であって、1〜3個の置換基で任意に置換されてもよく、前記置換基のうちの2つが隣接するときは、それらが結合する1つ以上の原子と共に、0〜6個のヘテロ環原子を有する5〜16員環を形成し得、
L2は結合、−(CRxRy)n−、−N=、−O−、−S−、−SO−、−SO2−、−CO−、−CO−O−、−O−CO−、−NRx−、−NRx−CO−、−NRx−SO2−、−CO−NRx−、−SO2−NRx−、−NRx−CO−O−、−NRx−SO2−O−、−NRx−CO−NRy−、−NRx−SO2−NRy−、−CO−NRx−NRy−、−SO2−NRx−NRy−、−NRx−CO−CO−O−、−NRx−SO2−SO2−O−、−S(O)2−Nx−CO−Ry−、−CO−Nx−S(O)2−Ry−又は−(NRxRy)C=N−O−であり、
Rcは水素、アルキル基、アルケニル基、アルキニル基、グアニジニル基、シクロアルキル基、ヘテロシクロアルキル基、シクロアルケニル基、ヘテロシクロアルケニル基、アリール基、ヘテロアリール基、(シクロアルキル)アルキル基、(ヘテロシクロアルキル)アルキル基、(シクロアルケニル)アルキル基、(ヘテロシクロアルケニル)アルキル基、アラルキル基又はヘテロアラルキル基であって、かつ、水素を除いて、1〜3個の置換基で任意に置換されてもよく、
Rx及びRyは各々独立に、水素、ヒドロキシ基、アルキル基、アルコキシ基、アミノ基、−CO−アルキル基、−CO−アリール基、−SO2−アルキル基、−SO2−アリール基、−SO2−ヘテロアリール基又は−P(O)(O−アルキル)2であり、
Rx又はRyのアルキル部分又はアリール部分は、1〜3個の置換基で任意に置換されてもよく、
R a 、R b 、R c 、R x 及びR y 上の前記1〜3個の任意の置換基が、各々独立に、アルキル基、アルケニル基、アルキニル基、シクロアルキル基、ヘテロシクロアルキル基、アリール基、ヘテロアリール基、アリールアルキル基、ヘテロアリールアルキル基、−OR、−SR、−NRR’、オキソ基、−C(O)−OR、−C(O)−NRR’、ハロ基、CN、NO 2 、N 3 、−C(O)R”、−P(O)(OR)(OR’)、−O−P(O)(OR)(OR’)、−NR−P(O)(OR)(OR’)、−S(O) 2 −OR、−O−S(O) 2 −OR、−NR−S(O) 2 −OR’、−NR−C(O)−OR”、−NR−C(O)−NRR’、−NR−C(S)−NRR’、−C(S)−NRR’及びチオアルキル基であり、
R及びR’が各々独立に、水素、アルキル基、シクロアルキル基、ヘテロシクロアルキル基、アリール基、ヘテロアリール基、アラルキル基又はヘテロアラルキル基であり、
R”がアルキル基、シクロアルキル基、ヘテロシクロアルキル基、アリール基、ヘテロアリール基、アラルキル基又はヘテロアラルキル基であり、
nは0、1、2、又は3である)。 Compounds of formula (I), prodrugs, polymorphs, tautomers, enantiomers, stereoisomers, solvates, N-oxide derivatives or pharmaceutically acceptable salts thereof :
Wherein R 1 is hydrogen or a halo group,
R 2 is -L 1 -R a,
L 1 is a bond or an alkyl group,
R a is a cyclohexyl group, a cycloheptyl group, a piperidinyl group, a pyrrolidinyl group, a furyl group, a thienyl group, a morpholinyl group, a pyridinyl group or a pyrimidinyl group, each of which may be optionally substituted with 1 to 3 substituents. Or
R a is a substituted phenyl group,
R 3 is -R b -L 2 -R c,
R b is an aryl group, heteroaryl group, cycloalkyl group or heterocycloalkyl group, which may be optionally substituted with 1 to 3 substituents, and when two of the substituents are adjacent to each other , together with one or more atoms to which they are attached, can form a 5 to 16-membered ring having 0-6 hetero ring atoms,
L 2 is a bond, — (CR x R y ) n —, —N═, —O—, —S— , —SO—, —SO 2 —, —CO—, —CO—O—, —O—CO. -, - NR x -, - NR x -CO -, - NR x -SO 2 -, - CO-NR x -, - SO 2 -NR x -, - NR x -CO-O -, - NR x - SO 2 -O -, - NR x -CO-NR y -, - NR x -SO 2 -NR y -, - CO-NR x -NR y -, - SO 2 -NR x -NR y -, - NR x -CO-CO-O -, - NR x -SO 2 -SO 2 -O -, - S (O) 2 -N x -CO-R y -, - CO-N x -S (O) 2 - R y — or — (NR x R y ) C═N—O—,
R c is hydrogen, an alkyl group, an alkenyl group, an alkynyl group, guanidinyl group, a cycloalkyl group, a heterocycloalkyl group, a cycloalkenyl group, a heterocycloalkenyl group, an aryl group, a heteroaryl group, (cycloalkyl) alkyl groups, ( Heterocycloalkyl) alkyl group, (cycloalkenyl) alkyl group, (heterocycloalkenyl) alkyl group, aralkyl group or heteroaralkyl group, and optionally substituted with 1 to 3 substituents, excluding hydrogen May be,
R x and R y are each independently hydrogen, hydroxy group, alkyl group, alkoxy group, amino group, —CO-alkyl group, —CO-aryl group, —SO 2 -alkyl group, —SO 2 -aryl group, -SO 2 - heteroaryl group or -P (O) (O-alkyl) 2,
The alkyl or aryl moiety of R x or R y may be optionally substituted with 1 to 3 substituents,
Any of the above 1 to 3 optional substituents on R a , R b , R c , R x and R y are each independently an alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, Aryl group, heteroaryl group, arylalkyl group, heteroarylalkyl group, —OR, —SR, —NRR ′, oxo group, —C (O) —OR, —C (O) —NRR ′, halo group, CN , NO 2 , N 3 , —C (O) R ″, —P (O) (OR) (OR ′), —O—P (O) (OR) (OR ′), —NR—P (O) (OR) (OR ′), —S (O) 2 —OR, —O—S (O) 2 —OR, —NR—S (O) 2 —OR ′, —NR—C (O) —OR ”. , -NR-C (O) -NRR ', -NR-C (S) -NRR', -C (S) -NRR 'and a thioalkyl group,
R and R ′ are each independently hydrogen, alkyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, aralkyl group or heteroaralkyl group,
R ″ is an alkyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an aralkyl group or a heteroaralkyl group,
n is 0, 1, 2, or 3 .
Rcが、テトラゾリル基、モリホリノ基又はピペラジニル基であって、任意に置換されてもよい、請求項1または10記載の化合物。 L 2 is a bond;
R c is, tetrazolyl group, a morpholino group or a piperazinyl group, it may be substituted by arbitrary claim 1 or 10 compound as described.
L2が結合であり、
Rcが水素である、請求項1記載の化合物。 R b is a phenyl group substituted with 1 to 3 substituents each independently selected from the group consisting of —NRR ′ and —C (O) OR;
L 2 is a bond;
The compound of claim 1, wherein R c is hydrogen.
R a がシクロヘプチル基、ピリジニル基、ピリミジニル基又はフェニル基であり、
R b が、1〜3個の置換基で置換されたフェニル基であり、
R3が4−(エトキシカルボニル)メチルフェニル基、4−(1−メチルピペリジン−4−イル)メチルフェニル基、4−カルボキシメチルフェニル基、((4−エチルピペリジン−1−イル)カルボニル)メチルフェニル基、4−((メチルカルボキサミド)メチル)フェニル基、4−((イソプロピルカルボキサミド)メチル)フェニル基、4−((エトキシカルボニル)イソプロピル)フェニル基、4−(カルボキシイソプロピル)フェニル基、4−(4−メチルピペラジン−1−イル)カルボニル)イソプロピルフェニル基、4−(メタンスルホニル)メチルフェニル基、3−クロロ−4−(メタンスルホニル)メチルフェニル基、4−(メタンスルホニル)(2−モルホリノエチル)アミノフェニル基、4−(メタンスルホニル)(2−ピペリジノエチル)アミノフェニル基、4−(メタンスルホニル)(2−ヒドロキシエチル)アミノフェニル基、4−(メタンスルホニル)イソプロピルアミノフェニル基、4−(メタンスルホニル)(2−ヒドロキシ−3−(ピペリジン−1−イル)プロピル)アミノフェニル基、4−(メタンスルホニル)(2−(ピロリジン−1−イル)エチル)アミノフェニル基、4−(プロパンスルホニル)カルバモイルフェニル基、4−(tert−ブタンスルホニル)カルバモイルフェニル基又は4−(エタンスルホニル)カルバモイルフェニル基である、請求項1〜13記載の化合物。 L 1 is a bond or methyl;
R a is a cycloheptyl group, a pyridinyl group, a pyrimidinyl group or a phenyl group;
R b is a phenyl group substituted with 1 to 3 substituents;
R 3 is 4- (ethoxycarbonyl) methylphenyl group, 4- (1-methylpiperidin-4-yl) methylphenyl group, 4-carboxymethylphenyl group, ((4-ethylpiperidin-1-yl) carbonyl) methyl Phenyl group, 4-((methylcarboxamido) methyl) phenyl group, 4-((isopropylcarboxamido) methyl) phenyl group, 4-((ethoxycarbonyl) isopropyl) phenyl group, 4- (carboxyisopropyl) phenyl group, 4- (4-methylpiperazin-1-yl) carbonyl) isopropylphenyl group, 4- (methanesulfonyl) methylphenyl group, 3-chloro-4- (methanesulfonyl) methylphenyl group, 4- (methanesulfonyl) (2-morpholino Ethyl) aminophenyl group, 4- (methanesulfonyl) (2-piperidinoethyl) aminophenyl group, 4- (methanesulfonyl) (2-hydroxyethyl) aminophenyl group, 4- (methanesulfonyl) isopropylaminophenyl group, 4- (methanesulfonyl) (2-hydroxy-3- ( Piperidin-1-yl) propyl) aminophenyl group, 4- (methanesulfonyl) (2- (pyrrolidin-1-yl) ethyl) aminophenyl group, 4- (propanesulfonyl) carbamoylphenyl group, 4- (tert-butane) sulfonyl) is a carbamoyl phenyl group or 4- (ethanesulfonyl) carbamoyl phenyl group, claims 1-13 compound according.
Raがシクロヘプチル基又はフェニル基であり、
Rbがフェニル基であり、
L2が結合であり、
Rcがテトラゾリル基、モリホリノ基又はピペラジニル基であって、かつ任意に置換されてもよい、請求項3記載の化合物。 L 1 is a bond,
R a is a cycloheptyl group or a phenyl group,
R b is a phenyl group,
L 2 is a bond;
The compound according to claim 3, wherein R c is a tetrazolyl group, a morpholino group or a piperazinyl group, and may be optionally substituted.
Raが、アルコキシル基で置換された、シクロヘプチル基、ピリジニル基、ピリミジニル基又はフェニル基であり、
Rbがフェニル基であり、
L2が−O−、−S−、−SO2−、−CO−、−CO−O−、−NRx−、−NRx−CO−、−NRx−SO2−、−NRx−CO−O−、−NRx−CO−NRy−又は−NRx−CO−CO−O−であって、
かつRxが水素、アルキル基、−CO−アルキル基、−SO2−アルキル基又は−SO2−アリール基であり、
Rcが水素、アルキル基又はアリール基である、請求項1記載の化合物。 L 1 is a bond,
R a is substituted with an alkoxyl group, a cycloheptyl group, pyridinyl group, pyrimidinyl group or a phenyl group,
R b is a phenyl group,
L 2 is -O -, - S -, - SO 2 -, - CO -, - CO-O -, - NR x -, - NR x -CO -, - NR x -SO 2 -, - NR x - CO—O—, —NR x —CO—NR y — or —NR x —CO—CO—O—,
And R x is hydrogen, an alkyl group, —CO-alkyl group, —SO 2 -alkyl group or —SO 2 -aryl group,
R c is hydrogen, an alkyl group or an aryl group, a compound according to claim 1.
Raがシクロヘプチル基又はフェニル基であり、
Rbがフェニル基であり、
L2が−CO−O−、−NRx−、−NRx−SO2−、−NRx−CO−O−又は−NRx−CO−NRy−であって、
かつRxが水素、アルキル基、−CO−アルキル基、−SO2−アルキル基又は−SO2−アリール基であり、
Rcが水素、アルキル基又はアリール基である、請求項1記載の化合物。 L 1 is a bond,
R a is a cycloheptyl group or a phenyl group,
R b is a phenyl group,
L 2 is —CO—O—, —NR x —, —NR x —SO 2 —, —NR x —CO—O— or —NR x —CO—NR y —,
And R x is hydrogen, an alkyl group, —CO-alkyl group, —SO 2 -alkyl group or —SO 2 -aryl group,
R c is hydrogen, an alkyl group or an aryl group, a compound according to claim 1.
Raがフェニル基であり、
Rbがフェニル基であり、
L2が−CO−O−、−NRx−、−NRx−SO2−、−NRx−CO−O−又は−NRx−CO−NRyであって、
かつRx及びRyが各々独立に、水素、アルキル基、−CO−アルキル基、−SO2−アルキル基又は−SO2−アリール基であり、
Rcが水素、アルキル基又はアリール基である、請求項1記載の化合物。 L 1 is an alkyl group,
R a is a phenyl group,
R b is a phenyl group,
L 2 is —CO—O—, —NR x —, —NR x —SO 2 —, —NR x —CO—O— or —NR x —CO—NR y ,
And R x and R y are each independently hydrogen, an alkyl group, —CO-alkyl group, —SO 2 -alkyl group or —SO 2 -aryl group,
R c is hydrogen, an alkyl group or an aryl group, a compound according to claim 1.
N−(4−(1−(3−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)−N−(メチルスルホニル)メタンスルホンアミド、N−(4−(1−(4−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)−N−(メチルスルホニル)メタンスルホンアミド、N−(4−(1−(4−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)シクロプロパンスルホンアミド、1−(4−メトキシフェニル)−N−(3−(4−メチルピペラジン−1−イル)フェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、2−ヒドロキシ−5−(1−(4−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)ベンズアルデヒド、エチル2−(4−(1−(4−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニルアミノ)−2−オキソアセテート、N−(2,3,5,6,8,9,11,12,14,15−デカヒドロベンゾ[b]−[1,4,7,10,13,16]ヘキサオキサシクロオクタデシン−18−イル)−1−(4−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、1−(4−メトキシフェニル)−N−(2,3,5,6,8,9,11,12−オクタヒドロベンゾ[b]−[1,4,7,10,13]ペンタオキサシクロペンタデシン−15−イル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、N−(4−(1−(4−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)−1−(メチルスルホニル)メタンスルホンアミド、3,3,3−トリフルオロ−N−(4−(1−(4−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)プロパン−1−スルホンアミド、
1−(4−メトキシフェニル)−N−(4−モルホリノフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、N−(4−(1H−1,2,4−トリアゾール−1−イル)フェニル)−1−(4−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、2−メトキシ−4−(1−(4−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェノール、N−(3,4−ジメトキシフェニル)−1−(4−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、1−(3−(1−(4−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)エタノール、N1−(1−(4−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イル)ベンゼン−1,4−ジアミン、N−(4−(1−(4−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)メタンスルホンアミド、4−(1−(4−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェノール、1−(4−メトキシフェニル)−N−(3,4,5−トリメトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、1−(4−メトキシフェニル)−N−(4−(4−(メチルスルホニル)ピペラジン−1−イル)フェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、
メチル−3−(4−(1−(4−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニルアミノ)−3−オキソプロパノエート、2−メトキシ−N−(4−(1−(4−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)アセトアミド、N−(3,4−ジヒドロ−2H−ベンゾ[b][1,4]ジオキセピン−7−イル)−1−(4−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、2−エトキシ−5−(1−(4−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェノール、2−(4−(1−(4−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)エタノール、N−(4−(1−(4−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)アセトアミド、2−(2−メトキシエトキシ)−N−(4−(1−(4−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)アセトアミド、ジエチル4−(1−(4−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)ベンジルホスホネート、1−(3−メトキシフェニル)−N−(4−(4−(メチルスルホニル)ピペラジン−1−イル)フェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、ジメチル−4−(1−(4−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニルホスホロアミデート、
N1−(1−(3−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イル)ベンゼン−1,4−ジアミン、1−(4−メトキシフェニル)−N−(4−(4−メチルピペラジン−1−イル)フェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、N−(3−メトキシフェニル)−1−(4−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、3−(1−(4−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェノール、1−(4−メトキシフェニル)−N−(4−(ピペリジン−1−イル)フェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、N1−ビス(4−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、メチル4−(1−(4−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニルカルバメート、2−(4−(1−(4−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニルアミノ)−2−オキソエチルアセテート、N−(2,3−ジヒドロベンゾ[b][1,4]ダイオキシン−6−イル)−1−(4−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、2−メトキシ−5−(1−(4−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェノール、
1−(4−メトキシフェニル)−N−(4−(メチルチオ)フェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、4−(1−(4−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)−2−メチルフェノール、2−メトキシ−4−(1−(3−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェノール、N−(3,4−ジメトキシフェニル)−1−(3−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、2−(2−メトキシエトキシ)−N−(4−(1−(4−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)アセトアミド、(E)−N’−(4−(1−(4−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)−N,N−ジメチルホルムイミダミド、2−メトキシ−5−(1−(3−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェノール、N−(2,2−ジメチルベンゾ[d][1,3]ジオキソール−5−イル)−1−(4−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、メチル2−ヒドロキシ−5−(1−(4−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)ベンゾアート、1−(4−メトキシフェニル)−N−(4−(メチルスルホニル)フェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、
3−(1−(3−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェノール、1−(3−メトキシフェニル)−N−(2,3,5,6,8,9,11,12−オクタヒドロベンゾ[b]−[1,4,7,10,13]ペンタオキサシクロペンタデシン−15−イル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、N−(ベンゾ[d][1,3]ジオキソール−5−イル)−1−(3−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、N−(4−(1−(4−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)−N−メチルメタンスルホンアミド、4−メトキシ−N−(4−(1−(4−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)ベンズアミド、N−(2,4−ジメトキシフェニル)−1−(3−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、1−(4−メトキシフェニル)−N−(ナフタレン−1−イル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、N−(4−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)−N−(メチルスルホニル)メタンスルホンアミド、N−(4−(1H−テトラゾール−5−イル)フェニル)−1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、N,N−ジメチル−4−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニルスルファミド、
N1−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イル)ベンゼン−1,4−ジアミン、3−クロロ−N−(4−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)プロパン−1−スルホンアミド、3−クロロ−N−(4−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)−プロピル−1,3−スルタム、1−シクロヘプチル−N−(4−(4−(メチルスルホニル)ピペラジン−1−イル)フェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、4−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)安息香酸、1−シクロヘプチル−N−(4−モルホリノフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、3−クロロ−N−(3−クロロプロピルスルホニル)−N−(4−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)プロパン−1−スルホンアミド、(4−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)(モリホリノ)メタノン、N1−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イル)ベンゼン−1,3−ジアミン、1−(4−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)グアニジン、
N−(4−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)メタンスルホンアミド、ジメチル4−(4−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)ピペラジン−1−イルホスホネート、(4−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)(4−エチルピペラジン−1−イル)メタノン、1−シクロヘプチル−N−(4−チオモルホリノフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、ジメチル4−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニルホスホロアミデート、1−シクロヘプチル−N−(4−(ピペラジン−1−イル)フェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、1−シクロヘプチル−N−(4−(1−メチル−1H−テトラゾール−5−イル)フェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、2−(4−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)エタノール、1−アリル−3−(4−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)尿素、N−(4−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)アセトアミド、
1−(4−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)−3−エチル尿素、1−(4−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)−3−プロピル尿素、1−シクロヘプチル−N−(4−(4−メチルピペラジン−1−イル)フェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、1−シクロヘプチル−N−(4−(2−メチル−2H−テトラゾール−5−イル)フェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、N−(4−(2−(2−クロロエチル)−2H−テトラゾール−5−イル)フェニル)−1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、N−(4−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)チオフェン−2−スルホンアミド、4−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)ベンゾニトリル、N−(3−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)−N−(メチルスルホニル)メタンスルホンアミド、1−シクロヘプチル−N−(4−(ピペリジン−1−イル)フェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、N−(4−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)−1−(メチルスルホニル)−N−(メチルスルホニルメチルスルホニル)メタンスルホンアミド、
1−シクロヘプチル−N−(4−(2−モルホリノエトキシ)フェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、N−(4−(1H−ピラゾール−1−イル)フェニル)−1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、N−(4−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)−N−(フェニルスルホニル)ベンゼンスルホンアミド、N−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イル)−1,1,1−トリフルオロ−N−(4−(1,1,1−トリフルオロ−N−(トリフルオロメチルスルホニル)メチルスルホンアミド)フェニル)メタン−スルホンアミド、N−(ベンゾ[d][1,3]ジオキソール−5−イル)−1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、2−(4−(4−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)ピペラジン−1−イル)エタノール、1−シクロヘプチル−N−フェニル−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、1−シクロヘプチル−N−(4−(2−ビニル−2H−テトラゾール−5−イル)フェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、エチル4−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)ベンゾアート、tert−ブチル4−(4−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)ピペラジン−1−カルボキシレート、
N−(4−(1−(4−メトキシ−2−メチルフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)−N−(メチルスルホニル)メタンスルホンアミド、1−(4−メトキシ−2−メチルフェニル)−N−(4−(4−(メチルスルホニル)ピペラジン−1−イル)フェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、1−(4−メトキシ−2−メチルフェニル)−N−(4−(4−メチルピペラジン−1−イル)フェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、N−(4−(1−(4−メトキシ−2−メチルフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)メタンスルホンアミド、1−(4−メトキシ−2−メチルフェニル)−N−(4−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、1−(4−メトキシ−2−メチルフェニル)−N−(4−(トリフルオロメトキシ)フェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、1−(4−メトキシ−2−メチルフェニル)−N−(4−(メチルチオ)フェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、2−メトキシ−5−(1−(4−メトキシ−2−メチルフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェノール、3−(6−(4−アミノフェニルアミノ)−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)フェノール、4−(6−(4−アミノフェニルアミノ)−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)フェノール、
4−(6−(4−モルホリノフェニルアミノ)−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)フェノール、5−(1−(3−ヒドロキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)−2−メトキシフェノール、5−(1−(4−ヒドロキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)−2−メトキシフェノール、N1−(1−(4−ヨードフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イル)ベンゼン−1,4−ジアミン、4−(4−(6−(4−アミノフェニルアミノ)−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)フェニル)ブト−3−イン−1−オール、4−(4−(6−(3,4−ジメトキシフェニルアミノ)−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)フェニル)ブト−3−イン−1−オール、N−(3,4−ジメトキシフェニル)−1−(4−ヨードフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、5−(1−(4−ヨードフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)−2−メトキシフェノール、1−(4−エチルフェニル)−N−(4−(ピペリジン−1−イル)フェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、1−(4−ヨードフェニル)−N−(4−(ピペリジン−1−イル)フェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、
1−ベンジル−N−(4−(ピペリジン−1−イル)フェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、1−(3−メトキシベンジル)−N−(4−(ピペラジン−1−イル)フェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、1−(3,4−ジメトキシベンジル)−N−(4−(ピペラジン−1−イル)フェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、tert−ブチル4−(4−(1−(3,5−ジメトキシベンジル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)ピペラジン−1−カルボキシレート、1−(3,5−ジメトキシベンジル)−N−(4−(ピペラジン−1−イル)フェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、tert−ブチル4−(4−(3−ブロモ−1−(3,4−ジメトキシベンジル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)ピペラジン−1−カルボキシレート、tert−ブチル4−(4−(1−(3,4−ジメトキシベンジル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)ピペラジン−1−カルボキシレート、1−(4−メトキシベンジル)−N−(4−(ピペラジン−1−イル)フェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、tert−ブチル4−(4−(1−(4−メトキシベンジル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)ピペラジン−1−カルボキシレート、
エチル2−(4−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)アセテート、1−シクロヘプチル−N−(4−((4−メチルピペラジン−1−イル)メチル)フェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、2−(4−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)酢酸、2−(4−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)−1−(4−エチルピペラジン−1−イル)エタノン、2−(4−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)−N−メチルアセトアミド、2−(4−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)−N−イソプロピルアセトアミド、エチル2−(4−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)−2−メチルプロパノエート、2−(4−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)−2−メチルプロパン酸、エチル2−(2−クロロ−4−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)アセテート、2−(2−クロロ−4−(1−シクロヘプチル−1H−ピラゾロ[3,4d]ピリミジン−6−イルアミノ)フェニル)酢酸、
2−(4−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)−2−メチル−1−(4−メチルピペラジン−1−イル)プロパン−1−オン、1−シクロヘプチル−N−(4−(メチルスルホニルメチル)フェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、N−(3−クロロ−4−(メチルスルホニルメチル)フェニル)−1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、N−(4−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)−N−(2−モルホリノエチル)メタンスルホンアミド、N−(4−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)−N−(2−(ピペリジン−1−イル)エチル)メタンスルホンアミド、N−(4−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)−N−(2−ヒドロキシエチル)メタンスルホンアミド、N−(4−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)−N−イソプロピルメタンスルホンアミド、N−(4−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)−N−(2−ヒドロキシ−3−(ピペリジン−1−イル)プロピル)メタンスルホンアミド、N−(4−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)−N−(2−(ピロリジン−1−イル)エチル)メタンスルホンアミド、
1−ブチル−N−(4−(ピペリジン−1−イル)フェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、1−イソプロピル−N−(4−(ピペリジン−1−イル)フェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、1−(シクロペンチルメチル)−N−(4−(ピペリジン−1−イル)フェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、(S)−N−(4−モルホリノフェニル)−1−(1−フェニルエチル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、1−((6−フルオロ−4H−ベンゾ[d][1,3]ダイオキシン−8−イル)メチル)−N−(4−モルホリノフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、1−(フラン−2−イルメチル)−N−(4−(ピペラジン−1−イル)フェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、エチル2−(6−(4−(ピペリジン−1−イル)フェニルアミノ)−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)アセテート、N−(4−モルホリノフェニル)−1−(ピリジン−2−イルメチル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、1−メチル−N−(4−(ピペリジン−1−イル)フェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、N−(4−モルホリノフェニル)−1−(1,2,3,4−テトラヒドロナフタレン−1−イル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、1−(1−ベンジルピペリジン−4−イル)−N−(4−モルホリノフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、又は、1−((4−メトキシ−3,5−ジメチルピリジン−2−イル)メチル)−N−(4−モルホリノフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、である、化合物。 The compound is
N- (4- (1- (3-methoxyphenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenyl) -N- (methylsulfonyl) methanesulfonamide, N- (4- ( 1- (4-methoxyphenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenyl) -N- (methylsulfonyl) methanesulfonamide, N- (4- (1- (4-methoxy Phenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenyl) cyclopropanesulfonamide, 1- (4-methoxyphenyl) -N- (3- (4-methylpiperazin-1-yl) Phenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, 2-hydroxy-5- (1- (4-methoxyphenyl) -1H-pyrazolo [3,4-d Pyrimidin-6-ylamino) benzaldehyde, ethyl 2- (4- (1- (4-methoxyphenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenylamino) -2-oxoacetate, N -(2,3,5,6,8,9,11,12,14,15-decahydrobenzo [b]-[1,4,7,10,13,16] hexaoxacyclooctadecine-18- Yl) -1- (4-methoxyphenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, 1- (4-methoxyphenyl) -N- (2,3,5,6,8, 9,11,12-octahydrobenzo [b]-[1,4,7,10,13] pentaoxacyclopentadecin-15-yl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine , N- (4- (1 (4-Methoxyphenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenyl) -1- (methylsulfonyl) methanesulfonamide, 3,3,3-trifluoro-N- (4- (1- (4-methoxyphenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenyl) propane-1-sulfonamide,
1- (4-methoxyphenyl) -N- (4-morpholinophenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, N- (4- (1H-1,2,4-triazole- 1-yl) phenyl) -1- (4-methoxyphenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, 2-methoxy-4- (1- (4-methoxyphenyl) -1H- Pyrazolo [3,4-d] pyrimidin-6-ylamino) phenol, N- (3,4-dimethoxyphenyl) -1- (4-methoxyphenyl) -1H-pyrazolo [3,4-d] pyrimidine-6 Amine, 1- (3- (1- (4-methoxyphenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenyl) ethanol, N 1 -(1- (4-methoxyphenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-yl) benzene-1,4-diamine, N- (4- (1- (4-methoxyphenyl)- 1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenyl) methanesulfonamide, 4- (1- (4-methoxyphenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) Phenol, 1- (4-methoxyphenyl) -N- (3,4,5-trimethoxyphenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, 1- (4-methoxyphenyl)- N- (4- (4- (methylsulfonyl) piperazin-1-yl) phenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine,
Methyl-3- (4- (1- (4-methoxyphenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenylamino) -3-oxopropanoate, 2-methoxy-N- (4- (1- (4-methoxyphenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenyl) acetamide, N- (3,4-dihydro-2H-benzo [b] [1 , 4] dioxepin-7-yl) -1- (4-methoxyphenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, 2-ethoxy-5- (1- (4-methoxyphenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenol, 2- (4- (1- (4-methoxyphenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) Fe ) Ethanol, N- (4- (1- (4-methoxyphenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenyl) acetamide, 2- (2-methoxyethoxy) -N- (4- (1- (4-methoxyphenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenyl) acetamide, diethyl 4- (1- (4-methoxyphenyl) -1H-pyrazolo [ 3,4-d] pyrimidin-6-ylamino) benzylphosphonate, 1- (3-methoxyphenyl) -N- (4- (4- (methylsulfonyl) piperazin-1-yl) phenyl) -1H-pyrazolo [3 , 4-d] pyrimidin-6-amine, dimethyl-4- (1- (4-methoxyphenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino Phenyl phosphoramidate,
N 1 -(1- (3-methoxyphenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-yl) benzene-1,4-diamine, 1- (4-methoxyphenyl) -N- (4- ( 4-methylpiperazin-1-yl) phenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, N- (3-methoxyphenyl) -1- (4-methoxyphenyl) -1H-pyrazolo [ 3,4-d] pyrimidin-6-amine, 3- (1- (4-methoxyphenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenol, 1- (4-methoxyphenyl) -N- (4- (piperidin-1-yl) phenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, N 1 -Bis (4-methoxyphenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, methyl Le 4 -(1- (4-methoxyphenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenylcarbamate, 2- (4- (1- (4-methoxyphenyl) -1H-pyrazolo [3 , 4-d] pyrimidin-6-ylamino) phenylamino) -2-oxoethyl acetate, N- (2,3-dihydrobenzo [b] [1,4] dioxin-6-yl) -1- (4- Methoxyphenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, 2-methoxy-5- (1- (4-methoxyphenyl) -1H-pyrazolo [3,4-d] pyrimidine-6- Ilamino) phenol,
1- (4-methoxyphenyl) -N- (4- (methylthio) phenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, 4- (1- (4-methoxyphenyl) -1H- Pyrazolo [3,4-d] pyrimidin-6-ylamino) -2-methylphenol, 2-methoxy-4- (1- (3-methoxyphenyl) -1H-pyrazolo [3,4-d] pyrimidine-6 Ylamino) phenol, N- (3,4-dimethoxyphenyl) -1- (3-methoxyphenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, 2- (2-methoxyethoxy) -N -(4- (1- (4-methoxyphenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenyl) acetamide, (E) -N '-(4- (1- (4- Methoxypheni ) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenyl) -N, N-dimethylformimidamide, 2-methoxy-5- (1- (3-methoxyphenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenol, N- (2,2-dimethylbenzo [d] [1,3] dioxol-5-yl) -1- (4-methoxyphenyl) -1H- Pyrazolo [3,4-d] pyrimidin-6-amine, methyl 2-hydroxy-5- (1- (4-methoxyphenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) benzoate, 1- (4-methoxyphenyl) -N- (4- (methylsulfonyl) phenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine,
3- (1- (3-methoxyphenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenol, 1- (3-methoxyphenyl) -N- (2,3,5,6, 8,9,11,12-octahydrobenzo [b]-[1,4,7,10,13] pentaoxacyclopentadecin-15-yl) -1H-pyrazolo [3,4-d] pyrimidine-6 -Amine, N- (benzo [d] [1,3] dioxol-5-yl) -1- (3-methoxyphenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, N- ( 4- (1- (4-methoxyphenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenyl) -N-methylmethanesulfonamide, 4-methoxy-N- (4- (1- (4-Methoxyphenyl) -1H- Lazolo [3,4-d] pyrimidin-6-ylamino) phenyl) benzamide, N- (2,4-dimethoxyphenyl) -1- (3-methoxyphenyl) -1H-pyrazolo [3,4-d] pyrimidine- 6-amine, 1- (4-methoxyphenyl) -N- (naphthalen-1-yl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, N- (4- (1-cycloheptyl- 1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenyl) -N- (methylsulfonyl) methanesulfonamide, N- (4- (1H-tetrazol-5-yl) phenyl) -1-cycloheptyl -1H-pyrazolo [3,4-d] pyrimidin-6-amine, N, N-dimethyl-4- (1-cycloheptyl-1H-pyrazolo [3,4-d] pyrimidine-6-i Amino) phenyl sulfamide,
N 1 -(1-cycloheptyl-1H-pyrazolo [3,4-d] pyrimidin-6-yl) benzene-1,4-diamine, 3-chloro-N- (4- (1-cycloheptyl-1H-pyrazolo [ 3,4-d] pyrimidin-6-ylamino) phenyl) propane-1-sulfonamide, 3-chloro-N- (4- (1-cycloheptyl-1H-pyrazolo [3,4-d] pyrimidine-6 Ylamino) phenyl) -propyl-1,3-sultam, 1-cycloheptyl-N- (4- (4- (methylsulfonyl) piperazin-1-yl) phenyl) -1H-pyrazolo [3,4-d] pyrimidine -6-amine, 4- (1-cycloheptyl-1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) benzoic acid, 1-cycloheptyl-N- (4-morpholinophenyl) 1H-pyrazolo [3,4-d] pyrimidin-6-amine, 3-chloro-N- (3-chloropropylsulfonyl) -N- (4- (1-cycloheptyl-1H-pyrazolo [3,4-d ] Pyrimidin-6-ylamino) phenyl) propane-1-sulfonamide, (4- (1-cycloheptyl-1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenyl) (morpholino) methanone, N 1 -(1-cycloheptyl-1H-pyrazolo [3,4-d] pyrimidin-6-yl) benzene-1,3-diamine, 1- (4- (1-cycloheptyl-1H-pyrazolo [3,4 d] pyrimidin-6-ylamino) phenyl) guanidine,
N- (4- (1-cycloheptyl-1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenyl) methanesulfonamide, dimethyl Le 4 -(4- (1-cycloheptyl-1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenyl) piperazin-1-ylphosphonate, (4- (1-cycloheptyl-1H-pyrazolo [3 4-d] pyrimidin-6-ylamino) phenyl) (4-ethylpiperazin-1-yl) methanone, 1-cycloheptyl-N- (4-thiomorpholinophenyl) -1H-pyrazolo [3,4-d] pyrimidine -6-amine, dimethyl Le 4 -(1-cycloheptyl-1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenyl phosphoramidate, 1-cycloheptyl-N- (4- (piperazin-1-yl) phenyl) -1H -Pyrazolo [3,4-d] pyrimidin-6-amine, 1-cycloheptyl-N- (4- (1-methyl-1H-tetrazol-5-yl) phenyl) -1H-pyrazolo [3,4-d ] Pyrimidin-6-amine, 2- (4- (1-cycloheptyl-1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenyl) ethanol, 1-allyl-3- (4- (1- Cycloheptyl-1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenyl) urea, N- (4- (1-cycloheptyl-1H-pyrazolo [3,4-d] pyrimidine-6- Arylamino) phenyl) acetamide,
1- (4- (1-cycloheptyl-1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenyl) -3-ethylurea, 1- (4- (1-cycloheptyl-1H-pyrazolo [ 3,4-d] pyrimidin-6-ylamino) phenyl) -3-propylurea, 1-cycloheptyl-N- (4- (4-methylpiperazin-1-yl) phenyl) -1H-pyrazolo [3,4 -D] pyrimidin-6-amine, 1-cycloheptyl-N- (4- (2-methyl-2H-tetrazol-5-yl) phenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine N- (4- (2- (2-chloroethyl) -2H-tetrazol-5-yl) phenyl) -1-cycloheptyl-1H-pyrazolo [3,4-d] pyrimidin-6-amine, N- ( 4- (1 Cycloheptyl-1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenyl) thiophene-2-sulfonamide, 4- (1-cycloheptyl-1H-pyrazolo [3,4-d] pyrimidine-6 Ylamino) benzonitrile, N- (3- (1-cycloheptyl-1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenyl) -N- (methylsulfonyl) methanesulfonamide, 1-cycloheptyl- N- (4- (piperidin-1-yl) phenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, N- (4- (1-cycloheptyl-1H-pyrazolo [3,4- d] pyrimidin-6-ylamino) phenyl) -1- (methylsulfonyl) -N- (methylsulfonylmethylsulfonyl) methanesulfonamide,
1-cycloheptyl-N- (4- (2-morpholinoethoxy) phenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, N- (4- (1H-pyrazol-1-yl) phenyl ) -1-cycloheptyl-1H-pyrazolo [3,4-d] pyrimidin-6-amine, N- (4- (1-cycloheptyl-1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) Phenyl) -N- (phenylsulfonyl) benzenesulfonamide, N- (1-cycloheptyl-1H-pyrazolo [3,4-d] pyrimidin-6-yl) -1,1,1-trifluoro-N- ( 4- (1,1,1-trifluoro-N- (trifluoromethylsulfonyl) methylsulfonamido) phenyl) methane-sulfonamide, N- (benzo [d] [1,3] dioxo- -5-yl) -1-cycloheptyl-1H-pyrazolo [3,4-d] pyrimidin-6-amine, 2- (4- (4- (1-cycloheptyl-1H-pyrazolo [3,4-d Pyrimidin-6-ylamino) phenyl) piperazin-1-yl) ethanol, 1-cycloheptyl-N-phenyl-1H-pyrazolo [3,4-d] pyrimidin-6-amine, 1-cycloheptyl-N- ( 4- (2-vinyl-2H-tetrazol-5-yl) phenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, ethyl 4- (1-cycloheptyl-1H-pyrazolo [3,4] -D] pyrimidin-6-ylamino) benzoate, tert-butyl 4- (4- (1-cycloheptyl-1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenyl) Perazine-1-carboxylate,
N- (4- (1- (4-methoxy-2-methylphenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenyl) -N- (methylsulfonyl) methanesulfonamide, 1- (4-methoxy-2-methylphenyl) -N- (4- (4- (methylsulfonyl) piperazin-1-yl) phenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, 1- (4-Methoxy-2-methylphenyl) -N- (4- (4-methylpiperazin-1-yl) phenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, N- (4- (1- (4-Methoxy-2-methylphenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenyl) methanesulfonamide, 1- (4-methoxy-2-methylphenyl)- -(4-Methoxyphenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, 1- (4-methoxy-2-methylphenyl) -N- (4- (trifluoromethoxy) phenyl)- 1H-pyrazolo [3,4-d] pyrimidin-6-amine, 1- (4-methoxy-2-methylphenyl) -N- (4- (methylthio) phenyl) -1H-pyrazolo [3,4-d] Pyrimidine-6-amine, 2-methoxy-5- (1- (4-methoxy-2-methylphenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenol, 3- (6- ( 4-aminophenylamino) -1H-pyrazolo [3,4-d] pyrimidin-1-yl) phenol, 4- (6- (4-aminophenylamino) -1H-pyrazolo [3,4-d] pyrimidine- 1 Yl) phenol,
4- (6- (4-morpholinophenylamino) -1H-pyrazolo [3,4-d] pyrimidin-1-yl) phenol, 5- (1- (3-hydroxyphenyl) -1H-pyrazolo [3,4 -D] pyrimidin-6-ylamino) -2-methoxyphenol, 5- (1- (4-hydroxyphenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) -2-methoxyphenol, N 1 -(1- (4-Iodophenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-yl) benzene-1,4-diamine, 4- (4- (6- (4-aminophenylamino) -1H-pyrazolo [3,4-d] pyrimidin-1-yl) phenyl) but-3-yn-1-ol, 4- (4- (6- (3,4-dimethoxyphenylamino) -1H-pyrazolo [3,4-d] pyrimidin-1-yl) phenyl) but-3-yn-1-ol, N- (3,4-dimethoxyphenyl) -1- (4-iodophenyl) -1H-pyrazolo [3 , 4-d] pyrimidin-6-amine, 5- (1- (4-iodophenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) -2-methoxyphenol, 1- (4- Ethylphenyl) -N- (4- (piperidi -1-yl) phenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, 1- (4-iodophenyl) -N- (4- (piperidin-1-yl) phenyl) -1H- Pyrazolo [3,4-d] pyrimidin-6-amine,
1-benzyl-N- (4- (piperidin-1-yl) phenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, 1- (3-methoxybenzyl) -N- (4- ( Piperazin-1-yl) phenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, 1- (3,4-dimethoxybenzyl) -N- (4- (piperazin-1-yl) phenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, tert-butyl 4- (4- (1- (3,5-dimethoxybenzyl) -1H-pyrazolo [3,4-d] pyrimidine-6 -Ylamino) phenyl) piperazine-1-carboxylate, 1- (3,5-dimethoxybenzyl) -N- (4- (piperazin-1-yl) phenyl) -1H-pyrazolo [3,4-d] pyrimidine- 6-a Tert-butyl 4- (4- (3-bromo-1- (3,4-dimethoxybenzyl) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenyl) piperazine-1-carboxylate , Tert-butyl 4- (4- (1- (3,4-dimethoxybenzyl) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenyl) piperazine-1-carboxylate, 1- (4 -Methoxybenzyl) -N- (4- (piperazin-1-yl) phenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, tert-butyl 4- (4- (1- (4- Methoxybenzyl) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenyl) piperazine-1-carboxylate,
Ethyl 2- (4- (1-cycloheptyl-1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenyl) acetate, 1-cycloheptyl-N- (4-((4-methylpiperazine-1 -Yl) methyl) phenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, 2- (4- (1-cycloheptyl-1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) ) Phenyl) acetic acid, 2- (4- (1-cycloheptyl-1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenyl) -1- (4-ethylpiperazin-1-yl) ethanone, -(4- (1-cycloheptyl-1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenyl) -N-methylacetamide, 2- (4- (1-cycloheptyl-1H Pyrazolo [3,4-d] pyrimidin-6-ylamino) phenyl) -N-isopropylacetamide, ethyl 2- (4- (1-cycloheptyl-1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) Phenyl) -2-methylpropanoate, 2- (4- (1-cycloheptyl-1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenyl) -2-methylpropanoic acid, ethyl 2- ( 2-chloro-4- (1-cycloheptyl-1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenyl) acetate, 2- (2-chloro-4- (1-cycloheptyl-1H-pyrazolo) [3,4d] pyrimidin-6-ylamino) phenyl) acetic acid,
2- (4- (1-Cycloheptyl-1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenyl) -2-methyl-1- (4-methylpiperazin-1-yl) propane-1- ON, 1-cycloheptyl-N- (4- (methylsulfonylmethyl) phenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, N- (3-chloro-4- (methylsulfonylmethyl) Phenyl) -1-cycloheptyl-1H-pyrazolo [3,4-d] pyrimidin-6-amine, N- (4- (1-cycloheptyl-1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) ) Phenyl) -N- (2-morpholinoethyl) methanesulfonamide, N- (4- (1-cycloheptyl-1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) pheny ) -N- (2- (piperidin-1-yl) ethyl) methanesulfonamide, N- (4- (1-cycloheptyl-1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenyl)- N- (2-hydroxyethyl) methanesulfonamide, N- (4- (1-cycloheptyl-1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenyl) -N-isopropylmethanesulfonamide, N -(4- (1-Cycloheptyl-1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenyl) -N- (2-hydroxy-3- (piperidin-1-yl) propyl) methanesulfonamide N- (4- (1-Cycloheptyl-1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenyl) -N- (2- (pyrrolidine-1 Yl) ethyl) methanesulfonamide,
1-butyl-N- (4- (piperidin-1-yl) phenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, 1-isopropyl-N- (4- (piperidin-1-yl) ) Phenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, 1- (cyclopentylmethyl) -N- (4- (piperidin-1-yl) phenyl) -1H-pyrazolo [3,4 d] pyrimidin-6-amine, (S) -N- (4-morpholinophenyl) -1- (1-phenylethyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, 1-(( 6-fluoro-4H-benzo [d] [1,3] dioxin-8-yl) methyl) -N- (4-morpholinophenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, 1 -(Fran-2-ilme ) -N- (4- (piperazin-1-yl) phenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, ethyl 2- (6- (4- (piperidin-1-yl) Phenylamino) -1H-pyrazolo [3,4-d] pyrimidin-1-yl) acetate, N- (4-morpholinophenyl) -1- (pyridin-2-ylmethyl) -1H-pyrazolo [3,4-d ] Pyrimidin-6-amine, 1-methyl-N- (4- (piperidin-1-yl) phenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, N- (4-morpholinophenyl) -1- (1,2,3,4-tetrahydronaphthalen-1-yl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, 1- (1-benzylpiperidin-4-yl) -N -(4-morpholinov Nyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine or 1-((4-methoxy-3,5-dimethylpyridin-2-yl) methyl) -N- (4-morpholinophenyl) ) -1H-pyrazolo [3,4-d] pyrimidin-6-amine , Compound object.
N−(4−(1H−テトラゾール−5−イル)フェニル)−1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、N−(4−(1H−テトラゾール−5−イル)フェニル)−1−(ビフェニル−2−イル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、N−(4−(1H−テトラゾール−5−イル)フェニル)−1−(3−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、N−(4−(1H−テトラゾール−5−イル)フェニル)−1−(4−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、1−シクロヘプチル−N−(4−モルホリノフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、1−(ビフェニル−2−イル)−N−(4−モルホリノフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、N−(4−モルホリノフェニル)−1−(フェナントレン−4−イル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、1−(3−メトキシフェニル)−N−(4−モルホリノフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、1−(4−メトキシフェニル)−N−(4−モルホリノフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、1−シクロヘプチル−N−(4−(ピペラジン−1−イル)フェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、1−(ビフェニル−2−イル)−N−(4−(ピペラジン−1−イル)フェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、1−(3−メトキシフェニル)−N−(4−(ピペラジン−1−イル)フェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、1−(4−メトキシフェニル)−N−(4−(ピペラジン−1−イル)フェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、4−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)安息香酸、4−(1−(ビフェニル−2−イル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)安息香酸、4−(1−(3−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)安息香酸、4−(1−(4−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)安息香酸、N1−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イル)ベンゼン−1,4−ジアミン、N1−(1−(ビフェニル−2−イル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イル)ベンゼン−1,4−ジアミン、N1−(1−(3−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イル)ベンゼン−1,4−ジアミン、N1−(1−(4−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イル)ベンゼン−1,4−ジアミン、N−(4−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)−N−(メチルスルホニル)メタンスルホンアミド、N−(4−(1−(ビフェニル−2−イル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)−N−(メチルスルホニル)メタンスルホンアミド、N−(4−(1−(3−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)−N−(メチルスルホニル)メタンスルホンアミド、N−(4−(1−(4−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)−N−(メチルスルホニル)メタンスルホンアミド、N−(4−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)メタンスルホンアミド、N−(4−(1−(ビフェニル−2−イル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)メタンスルホンアミド、N−(4−(1−(フェナントレン−4−イル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)メタンスルホンアミド、N−(4−(1−(3−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)メタンスルホンアミド、N−(4−(1−(4−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)メタンスルホンアミド、1−シクロヘプチル−N−(4−(4−メチルピペラジン−1−イル)フェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、1−(ビフェニル−2−イル)−N−(4−(4−メチルピペラジン−1−イル)フェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、1−(3−メトキシフェニル)−N−(4−(4−メチルピペラジン−1−イル)フェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、1−(4−メトキシフェニル)−N−(4−(4−メチルピペラジン−1−イル)フェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、5−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)−2−メトキシフェノール、5−(1−(ビフェニル−2−イル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)−2−メトキシフェノール、2−メトキシ−5−(1−(3−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェノール、4−(6−(4−(N−(メチルスルホニル)メチルスルホンアミド)フェニルアミノ)−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)フェニル二水素ホスフェート、4−メトキシ−N1−(1−(4−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イル)ベンゼン−1,3−ジアミン、4−(6−(4−(N−(メチルスルホニル)メチルスルホンアミド)フェニルアミノ)−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)フェニルアセテート、4−(6−(4−(N−(メチルスルホニル)メチルスルホンアミド)フェニルアミノ)−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)フェニルスルファメート、N−(4−(1−(4−ヒドロキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)−N−(メチルスルホニル)メタンスルホンアミド、2−メトキシ−5−(1−(4−メトキシフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェノール、1−(シクロペンチルメチル)−N−(4−(ピペリジン−1−イル)フェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、(S)−N−(4−モルホリノフェニル)−1−(1−フェニルエチル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、1−((6−フルオロ−4H−ベンゾ[d][1,3]ダイオキシン−8−イル)メチル)−N−(4−モルホリノフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、1−(フラン−2−イルメチル)−N−(4−(ピペラジン−1−イル)フェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、N−(4−モルホリノフェニル)−1−(ピリジン−2−イルメチル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、1−(1−ベンジルピペリジン−4−イル)−N−(4−モルホリノフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、1−((4−メトキシ−3,5−ジメチルピリジン−2−イル)メチル)−N−(4−モルホリノフェニル)−1H−ピラゾロ[3,4−d]ピリミジン−6−アミン、N−(5−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)ピリジン−2−イル)−N−(メチルスルホニル)メタンスルホンアミド、N−(5−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)ピリジン−2−イル)メタンスルホンアミド、N−(5−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)ピリジン−2−イル)−N−(2−ヒドロキシエチル)メタンスルホンアミド、N−(4−(6−(6−(N−(メチルスルホニル)メチルスルホンアミド)ピリジン−3−イルアミノ)−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)フェニル)−2−(ピロリジン−1−イル)アセトアミド、N−(4−(6−(6−(メチルスルホンアミド)ピリジン−3−イルアミノ)−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)フェニル)−2−(ピロリジン−1−イル)アセトアミド、N−(5−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)ピリジン−2−イル)−N−(2−モルホリノエチル)メタンスルホンアミド、N−(5−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)ピリジン−2−イル)−N−(2,3−ジヒドロキシプロピル)メタンスルホンアミド、N−(4−(6−(6−(N−(2,3−ジヒドロキシプロピル)メチルスルホンアミド)ピリジン−3−イルアミノ)−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)フェニル)−2−(ピロリジン−1−イル)アセトアミド、tert−ブチル4−(6−(6−(N−(2,3−ジヒドロキシプロピル)メチルスルホンアミド)ピリジン−3−イルアミノ)−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)フェニルカルバメート、tert−ブチル4−(6−(6−(N−(2−モルホリノエチル)メチルスルホンアミド)ピリジン−3−イルアミノ)−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)フェニルカルバメート、N−(5−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)ピリミジン−2−イル)メタンスルホンアミド、N−(5−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)ピリミジン−2−イル)−N−(2,3−ジヒドロキシプロピル)メタンスルホンアミド、
tert−ブチル4−(6−(2−(N−(2,3−ジヒドロキシプロピル)メチルスルホンアミド)ピリミジン−5−イルアミノ)−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)フェニルカルバメート、N−(5−(1−シクロヘプチル−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)ピリミジン−2−イル)−N−(2−モルホリノエチル)メタンスルホンアミド、N−(4−(6−(2−(N−(2,3−ジヒドロキシプロピル)メチルスルホンアミド)ピリミジン−5−イルアミノ)−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)フェニル)−2−(ピロリジン−1−イル)アセトアミド、tert−ブチル4−(6−(2−(N−(2−モルホリノエチル)メチルスルホンアミド)ピリミジン−5−イルアミノ)−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)フェニルカルバメート、tert−ブチル5−(6−(2−(N−(2−モルホリノエチル)メチルスルホンアミド)ピリミジン−5−イルアミノ)−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)ピリジン−2−イルカルバメート、N−(5−(6−(2−(N−(2,3−ジヒドロキシプロピル)メチルスルホンアミド)ピリミジン−5−イルアミノ)−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)ピリジン−2−イル)−2−(ピロリジン−1−イル)アセトアミド、N−(5−(6−(6−(N−(2,3−ジヒドロキシプロピル)メチルスルホンアミド)ピリジン−3−イルアミノ)−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)ピリジン−2−イル)−2−(ピロリジン−1−イル)アセトアミド、tert−ブチル5−(6−(6−(N−(2−モルホリノエチル)メチルスルホンアミド)ピリジン−3−イルアミノ)−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)ピリジン−2−イルカルバメート、tert−ブチル6−(6−(6−(N−(2−モルホリノエチル)メチルスルホンアミド)ピリジン−3−イルアミノ)−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)ピリジン−3−イルカルバメート、N−(6−(6−(6−(N−(2,3−ジヒドロキシプロピル)メチルスルホンアミド)ピリジン−3−イルアミノ)−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)ピリジン−3−イル)−2−(ピロリジン−1−イル)アセトアミド、tert−ブチル6−(6−(2−(N−(2,3−ジヒドロキシプロピル)メチルスルホンアミド)ピリミジン−5−イルアミノ)−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)ピリジン−3−イルカルバメート、tert−ブチル6−(6−(6−(N−(2,3−ジヒドロキシプロピル)メチルスルホンアミド)ピリジン−3−イルアミノ)−1H−ピラゾロ[3,4−d]ピリミジン−1−イル)ピリジン−3−イルカルバメート、N−(5−(1−(3−ヒドロキシベンジル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)ピリジン−2−イル)メタンスルホンアミド、N−(2,3−ジヒドロキシプロピル)−N−(5−(1−(3−ヒドロキシベンジル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)ピリジン−2−イル)メタンスルホンアミド、N−(2,3−ジヒドロキシプロピル)−N−(5−(1−(2−ヒドロキシピリジン−4−イル)メチル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)ピリジン−2−イル)メタンスルホンアミド、N−(5−(1−(3−ヒドロキシベンジル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)ピリジン−2−イル)−N−(2−モルホリノエチル)メタンスルホンアミド、N−(2,3−ジヒドロキシプロピル)−N−(4−(1−((2−ヒドロキシピリジン−4−イル)メチル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)フェニル)メタンスルホンアミド、又は、N−(5−(1−((2−ヒドロキシピリジン−4−イル)メチル)−1H−ピラゾロ[3,4−d]ピリミジン−6−イルアミノ)ピリジン−2−イル)−N−(2−モルホリノエチル)メタンスルホンアミド、である、請求項1記載の化合物。 The compound is
N- (4- (1H-tetrazol-5-yl) phenyl) -1-cycloheptyl-1H-pyrazolo [3,4-d] pyrimidin-6-amine, N- (4- (1H-tetrazol-5- Yl) phenyl) -1- (biphenyl-2-yl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, N- (4- (1H-tetrazol-5-yl) phenyl) -1- (3-methoxyphenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, N- (4- (1H-tetrazol-5-yl) phenyl) -1- (4-methoxyphenyl) -1H -Pyrazolo [3,4-d] pyrimidin-6-amine, 1-cycloheptyl-N- (4-morpholinophenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, 1- (biphenyl- 2-Ile) N- (4-morpholinophenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, N- (4-morpholinophenyl) -1- (phenanthren-4-yl) -1H-pyrazolo [3 4-d] pyrimidin-6-amine, 1- (3-methoxyphenyl) -N- (4-morpholinophenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, 1- (4-methoxy Phenyl) -N- (4-morpholinophenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, 1-cycloheptyl-N- (4- (piperazin-1-yl) phenyl) -1H- Pyrazolo [3,4-d] pyrimidin-6-amine, 1- (biphenyl-2-yl) -N- (4- (piperazin-1-yl) phenyl) -1H-pyrazolo [3,4-d] pyrimidine − -Amine, 1- (3-methoxyphenyl) -N- (4- (piperazin-1-yl) phenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, 1- (4-methoxyphenyl) ) -N- (4- (piperazin-1-yl) phenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, 4- (1-cycloheptyl-1H-pyrazolo [3,4-d ] Pyrimidin-6-ylamino) benzoic acid, 4- (1- (biphenyl-2-yl) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) benzoic acid, 4- (1- (3- Methoxyphenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) benzoic acid, 4- (1- (4-methoxyphenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino ) Benzoic acid, N 1 - (1-cycloheptyl -1H- pyrazolo [3,4-d] pyrimidin-6-yl) benzene-1,4-diamine, N 1 - (1- (biphenyl-2-yl) -1H- pyrazolo [ 3,4-d] pyrimidin-6-yl) benzene-1,4-diamine, N 1 - (1- (3- methoxyphenyl) -1H- pyrazolo [3,4-d] pyrimidin-6-yl) benzene 1,4-diamine, N 1 - (1- (4- methoxyphenyl) -1H- pyrazolo [3,4-d] pyrimidin-6-yl) benzene-1,4-diamine, N- (4- ( 1-cycloheptyl-1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenyl) -N- (methylsulfonyl) methanesulfonamide, N- (4- (1- (biphenyl-2-yl)- 1H-pyrazolo [3 -D] pyrimidin-6-ylamino) phenyl) -N- (methylsulfonyl) methanesulfonamide, N- (4- (1- (3-methoxyphenyl) -1H-pyrazolo [3,4-d] pyrimidine-6 -Ylamino) phenyl) -N- (methylsulfonyl) methanesulfonamide, N- (4- (1- (4-methoxyphenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenyl)- N- (methylsulfonyl) methanesulfonamide, N- (4- (1-cycloheptyl-1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenyl) methanesulfonamide, N- (4- (1 -(Biphenyl-2-yl) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenyl) methanesulfonamide, N- (4- ( 1- (phenanthren-4-yl) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenyl) methanesulfonamide, N- (4- (1- (3-methoxyphenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenyl) methanesulfonamide, N- (4- (1- (4-methoxyphenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) Phenyl) methanesulfonamide, 1-cycloheptyl-N- (4- (4-methylpiperazin-1-yl) phenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, 1- (biphenyl- 2-yl) -N- (4- (4-methylpiperazin-1-yl) phenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, 1- (3-methoxy Enyl) -N- (4- (4-methylpiperazin-1-yl) phenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, 1- (4-methoxyphenyl) -N- (4 -(4-Methylpiperazin-1-yl) phenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, 5- (1-cycloheptyl-1H-pyrazolo [3,4-d] pyrimidine- 6-ylamino) -2-methoxyphenol, 5- (1- (biphenyl-2-yl) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) -2-methoxyphenol, 2-methoxy-5 -(1- (3-methoxyphenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenol, 4- (6- (4- (N- (methylsulfonyl) methylsulfonamide) Eniruamino) -1H- pyrazolo [3,4-d] pyrimidin-1-yl) phenyl dihydrogen phosphate, 4-methoxy-N1- (1-(4-methoxyphenyl) -1H- pyrazolo [3,4-d] Pyrimidin-6-yl) benzene-1,3-diamine , 4- (6- (4- (N- (methylsulfonyl) methylsulfonamido) phenylamino) -1H-pyrazolo [3,4-d] pyrimidine-1 -Yl) phenyl acetate , 4- (6- (4- (N- (methylsulfonyl) methylsulfonamido) phenylamino) -1H-pyrazolo [3,4-d] pyrimidin-1-yl) phenylsulfamate , N- (4- (1- (4-hydroxyphenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenyl) -N- (methylsulfo ) Methanesulfonamide, 2-methoxy-5- (1- (4-methoxyphenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenol, 1- (cyclopentylmethyl) -N- ( 4- (piperidin-1-yl) phenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, (S) -N- (4-morpholinophenyl) -1- (1-phenylethyl)- 1H-pyrazolo [3,4-d] pyrimidin-6-amine, 1-((6-fluoro-4H-benzo [d] [1,3] dioxin-8-yl) methyl) -N- (4-morpholino Phenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, 1- (furan-2-ylmethyl) -N- (4- (piperazin-1-yl) phenyl) -1H-pyrazolo [3 4-d] Pyrimidin-6-amine, N- (4-morpholinophenyl) -1- (pyridin-2-ylmethyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, 1- (1-benzylpiperidine-4 -Yl) -N- (4-morpholinophenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, 1-((4-methoxy-3,5-dimethylpyridin-2-yl) methyl) -N- (4-morpholinophenyl) -1H-pyrazolo [3,4-d] pyrimidin-6-amine, N- (5- (1-cycloheptyl-1H-pyrazolo [3,4-d] pyrimidine-6 -Ylamino) pyridin-2-yl) -N- (methylsulfonyl) methanesulfonamide, N- (5- (1-cycloheptyl-1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) pi Gin-2-yl) methanesulfonamide, N- (5- (1-cycloheptyl-1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) pyridin-2-yl) -N- (2-hydroxy Ethyl) methanesulfonamide, N- (4- (6- (6- (N- (methylsulfonyl) methylsulfonamido) pyridin-3-ylamino) -1H-pyrazolo [3,4-d] pyrimidin-1-yl ) Phenyl) -2- (pyrrolidin-1-yl) acetamide, N- (4- (6- (6- (methylsulfonamido) pyridin-3-ylamino) -1H-pyrazolo [3,4-d] pyrimidine- 1-yl) phenyl) -2- (pyrrolidin-1-yl) acetamide, N- (5- (1-cycloheptyl-1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) Pyridin-2-yl) -N- (2-morpholinoethyl) methanesulfonamide, N- (5- (1-cycloheptyl-1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) pyridine-2- Yl) -N- (2,3-dihydroxypropyl) methanesulfonamide, N- (4- (6- (6- (N- (2,3-dihydroxypropyl) methylsulfonamido) pyridin-3-ylamino)- 1H-pyrazolo [3,4-d] pyrimidin-1-yl) phenyl) -2- (pyrrolidin-1-yl) acetamide, tert-butyl 4- (6- (6- (N- (2,3-dihydroxy) Propyl) methylsulfonamido) pyridin-3-ylamino) -1H-pyrazolo [3,4-d] pyrimidin-1-yl) phenylcarbamate, tert-butyl 4- (6- (6- (N- (2-morpholinoethyl) methylsulfonamido) pyridin-3-ylamino) -1H-pyrazolo [3,4-d] pyrimidin-1-yl) phenylcarbamate, N- (5- (1-Cycloheptyl-1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) pyrimidin-2-yl) methanesulfonamide, N- (5- (1-cycloheptyl-1H-pyrazolo [3,4] -D] pyrimidin-6-ylamino) pyrimidin-2-yl) -N- (2,3-dihydroxypropyl) methanesulfonamide,
tert-Butyl 4- (6- (2- (N- (2,3-dihydroxypropyl) methylsulfonamido) pyrimidin-5-ylamino) -1H-pyrazolo [3,4-d] pyrimidin-1-yl) phenyl Carbamate, N- (5- (1-cycloheptyl-1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) pyrimidin-2-yl) -N- (2-morpholinoethyl) methanesulfonamide, N- (4- (6- (2- (N- (2,3-dihydroxypropyl) methylsulfonamido) pyrimidin-5-ylamino) -1H-pyrazolo [3,4-d] pyrimidin-1-yl) phenyl)- 2- (pyrrolidin-1-yl) acetamide, tert-butyl 4- (6- (2- (N- (2-morpholinoethyl) methylsulfonamido) pyrimidine) 5-ylamino) -1H-pyrazolo [3,4-d] pyrimidin-1-yl) phenylcarbamate, tert-butyl 5- (6- (2- (N- (2-morpholinoethyl) methylsulfonamido) pyrimidine- 5-ylamino) -1H-pyrazolo [3,4-d] pyrimidin-1-yl) pyridin-2-ylcarbamate, N- (5- (6- (2- (N- (2,3-dihydroxypropyl)) Methylsulfonamido) pyrimidin-5-ylamino) -1H-pyrazolo [3,4-d] pyrimidin-1-yl) pyridin-2-yl) -2- (pyrrolidin-1-yl) acetamide, N- (5- (6- (6- (N- (2,3-dihydroxypropyl) methylsulfonamido) pyridin-3-ylamino) -1H-pyrazolo [3,4-d] pyrimidine-1 Yl) pyridin-2-yl) -2- (pyrrolidin-1-yl) acetamide, tert-butyl 5- (6- (6- (N- (2-morpholinoethyl) methylsulfonamido) pyridin-3-ylamino) -1H-pyrazolo [3,4-d] pyrimidin-1-yl) pyridin-2-ylcarbamate, tert-butyl 6- (6- (6- (N- (2-morpholinoethyl) methylsulfonamido) pyridine- 3-ylamino) -1H-pyrazolo [3,4-d] pyrimidin-1-yl) pyridin-3-ylcarbamate, N- (6- (6- (6- (N- (2,3-dihydroxypropyl)) Methylsulfonamido) pyridin-3-ylamino) -1H-pyrazolo [3,4-d] pyrimidin-1-yl) pyridin-3-yl) -2- (pyrrolidin-1-yl) ) Acetamide, tert-butyl 6- (6- (2- (N- (2,3-dihydroxypropyl) methylsulfonamido) pyrimidin-5-ylamino) -1H-pyrazolo [3,4-d] pyrimidine-1- Yl) pyridin-3-ylcarbamate, tert-butyl 6- (6- (6- (N- (2,3-dihydroxypropyl) methylsulfonamido) pyridin-3-ylamino) -1H-pyrazolo [3,4 d] pyrimidin-1-yl) pyridin-3-ylcarbamate, N- (5- (1- (3-hydroxybenzyl) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) pyridin-2- Yl) methanesulfonamide, N- (2,3-dihydroxypropyl) -N- (5- (1- (3-hydroxybenzyl) -1H-pyrazolo [3 -D] pyrimidin-6-ylamino) pyridin-2-yl) methanesulfonamide, N- (2,3-dihydroxypropyl) -N- (5- (1- (2-hydroxypyridin-4-yl) methyl) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) pyridin-2-yl) methanesulfonamide, N- (5- (1- (3-hydroxybenzyl) -1H-pyrazolo [3,4 d] pyrimidin-6-ylamino) pyridin-2-yl) -N- (2-morpholinoethyl) methanesulfonamide, N- (2,3-dihydroxypropyl) -N- (4- (1-((2- Hydroxypyridin-4-yl) methyl) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) phenyl) methanesulfonamide, or N- (5- (1-((2 Hydroxypyridin-4-yl) methyl) -1H-pyrazolo [3,4-d] pyrimidin-6-ylamino) pyridin-2-yl) -N- (2-morpholinoethyl) methanesulfonamide. 1. The compound according to 1.
The tumor or cancer is bone cancer, brain and CNS tumor, breast cancer, breast cancer, colorectal cancer, endocrine cancer, gastrointestinal cancer, urogenital cancer, gynecological cancer, head and neck cancer, leukemia, lung cancer, lymphoma 31. The composition of claim 30 , wherein the composition is ocular cancer, skin cancer, soft tissue sarcoma, urinary cancer, and other types or related disorders .
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US89830007P | 2007-01-30 | 2007-01-30 | |
US89838207P | 2007-01-30 | 2007-01-30 | |
PCT/US2008/001230 WO2008094602A2 (en) | 2007-01-30 | 2008-01-30 | 1-h-pyrazolo (3,4b) pyrimidine derivatives and their use as modulators of mitotic kinases |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2010532312A JP2010532312A (en) | 2010-10-07 |
JP2010532312A5 true JP2010532312A5 (en) | 2012-04-05 |
Family
ID=39469519
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2009548286A Withdrawn JP2010516812A (en) | 2007-01-30 | 2008-01-30 | Mitotic kinase modulators |
JP2009548293A Withdrawn JP2010532312A (en) | 2007-01-30 | 2008-01-30 | 1-H-pyrazolo (3,4B) pyrimidine derivatives and their use as modulators of mitotic kinases |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2009548286A Withdrawn JP2010516812A (en) | 2007-01-30 | 2008-01-30 | Mitotic kinase modulators |
Country Status (6)
Country | Link |
---|---|
US (2) | US20100190787A1 (en) |
EP (2) | EP2108020A2 (en) |
JP (2) | JP2010516812A (en) |
AU (2) | AU2008211108A1 (en) |
CA (2) | CA2676665A1 (en) |
WO (2) | WO2008094602A2 (en) |
Families Citing this family (52)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2010516812A (en) * | 2007-01-30 | 2010-05-20 | バイオジェン・アイデック・エムエイ・インコーポレイテッド | Mitotic kinase modulators |
TWI490214B (en) | 2008-05-30 | 2015-07-01 | 艾德克 上野股份有限公司 | Benzene or thiophene derivative and use thereof as vap-1 inhibitor |
HUE028347T2 (en) | 2008-06-10 | 2016-12-28 | Abbvie Inc | Tricyclic compounds |
CN102356083B (en) * | 2009-03-20 | 2014-10-15 | 内尔维阿诺医学科学有限公司 | Use of kinase inhibitor for treatment of thymoma |
TW201100441A (en) | 2009-06-01 | 2011-01-01 | Osi Pharm Inc | Amino pyrimidine anticancer compounds |
CA2775009A1 (en) | 2009-10-20 | 2011-04-28 | Cellzome Limited | Heterocyclyl pyrazolopyrimidine analogues as jak inhibitors |
PE20130005A1 (en) | 2009-12-01 | 2013-02-16 | Abbvie Inc | NEW TRICYCLIC COMPOUNDS |
BR112012013349B1 (en) | 2009-12-01 | 2019-10-22 | Abbott Lab | tricyclic compounds |
KR20130094693A (en) | 2010-04-30 | 2013-08-26 | 셀좀 리미티드 | Pyrazole compounds as jak inhibitors |
US8637529B2 (en) | 2010-06-11 | 2014-01-28 | AbbYie Inc. | Pyrazolo[3,4-d]pyrimidine compounds |
JP2013534233A (en) * | 2010-08-20 | 2013-09-02 | セルゾーム リミティッド | Heterocyclylpyrazolopyrimidine analogs as selective JAK inhibitors |
KR20140009259A (en) * | 2010-11-19 | 2014-01-22 | 에프. 호프만-라 로슈 아게 | Pyrazolopyridines and pyrazolopyridines and their use as tyk2 inhibitors |
ES2645508T3 (en) | 2010-11-29 | 2017-12-05 | OSI Pharmaceuticals, LLC | Macrocyclic Kinase Inhibitors |
WO2012143320A1 (en) | 2011-04-18 | 2012-10-26 | Cellzome Limited | (7h-pyrrolo[2,3-d]pyrimidin-2-yl)amine compounds as jak3 inhibitors |
WO2013017479A1 (en) * | 2011-07-29 | 2013-02-07 | Cellzome Limited | Pyrazolo[4,3-c]pyridine derivatives as jak inhibitors |
WO2013017480A1 (en) * | 2011-07-29 | 2013-02-07 | Cellzome Limited | Pyrazolo[4,3-c]pyridine derivatives as jak inhibitors |
ES2586213T3 (en) | 2011-10-31 | 2016-10-13 | Xenon Pharmaceuticals Inc. | Benzenesulfonamide compounds and their use as therapeutic agents |
KR20140105445A (en) | 2011-10-31 | 2014-09-01 | 제논 파마슈티칼스 인크. | Biaryl ether sulfonamides and their use as therapeutic agents |
CN103930425B (en) * | 2012-05-14 | 2016-04-27 | 华东理工大学 | Pteridinone derivative and the application as EGFR, BLK, FLT3 inhibitor thereof |
EA026393B1 (en) | 2012-05-22 | 2017-04-28 | Дженентек, Инк. | N-substituted benzamides and their use in the treatment of pain |
JP6309519B2 (en) | 2012-07-06 | 2018-04-11 | ジェネンテック, インコーポレイテッド | N-substituted benzamide and method of using the same |
WO2014071298A1 (en) | 2012-11-05 | 2014-05-08 | Nant Holdings Ip, Llc | Cyclic sulfonamide containing derivatives as inhibitors of hedgehog signaling pathway |
EP2968280A4 (en) | 2013-03-14 | 2016-08-10 | Genentech Inc | Substituted triazolopyridines and methods of use thereof |
US9493429B2 (en) | 2013-03-15 | 2016-11-15 | Genentech, Inc. | Substituted benzoxazoles and methods of use thereof |
MX2016006936A (en) | 2013-11-27 | 2016-10-05 | Genentech Inc | Substituted benzamides and methods of use thereof. |
CN106715418A (en) | 2014-07-07 | 2017-05-24 | 基因泰克公司 | Therapeutic compounds and methods of use thereof |
US10934291B2 (en) | 2014-09-25 | 2021-03-02 | Duke University | Kinase inhibitors and related methods of use |
GB201501115D0 (en) | 2015-01-23 | 2015-03-11 | Univ Dundee | Compounds |
CN107406452B (en) | 2015-01-23 | 2019-07-23 | 葛兰素史密斯克莱知识产权发展有限公司 | Pyrazolo [3,4-d] pyrimidine derivatives and its purposes for treating leishmaniasis |
CN107835805A (en) | 2015-05-22 | 2018-03-23 | 基因泰克公司 | Substituted benzamide and its application method |
WO2017035271A1 (en) | 2015-08-27 | 2017-03-02 | Genentech, Inc. | Therapeutic compounds and methods of use thereof |
JP6987746B2 (en) | 2015-09-28 | 2022-01-05 | ジェネンテック, インコーポレイテッド | Therapeutic compounds and their usage |
US11524964B2 (en) | 2015-10-16 | 2022-12-13 | Abbvie Inc. | Processes for the preparation of (3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]-pyrazin-8-yl)-n-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide and solid state forms thereof |
US11512092B2 (en) | 2015-10-16 | 2022-11-29 | Abbvie Inc. | Processes for the preparation of (3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]-pyrazin-8-yl)-n-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide and solid state forms thereof |
SG11201802990RA (en) | 2015-10-16 | 2018-05-30 | Abbvie Inc | PROCESSES FOR THE PREPARATION OF (3S,4R)-3-ETHYL-4-(3H-IMIDAZO[1,2-a]PYRROLO[2,3-e]-PYRAZIN-8-YL)-N-(2,2,2-TRIFLUOROETHYL)PYRROLIDINE-1-CARBOXAMIDE AND SOLID STATE FORMS THEREOF |
US10550126B2 (en) | 2015-10-16 | 2020-02-04 | Abbvie Inc. | Processes for the preparation of (3S,4R)-3-ethyl-4-(3H-imidazo[1,2-A]pyrrolo[2,3-e]-pyrazin-8-yl)-N-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide and solid state forms thereof |
US11365198B2 (en) | 2015-10-16 | 2022-06-21 | Abbvie Inc. | Processes for the preparation of (3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]-pyrazin-8-yl)-N-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide and solid state forms thereof |
US11780848B2 (en) | 2015-10-16 | 2023-10-10 | Abbvie Inc. | Processes for the preparation of (3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]-pyrazin-8-yl)-n-(2,2,2-trifluoroethyl)pyrrolidine-1- carboxamide and solid state forms thereof |
EP3380466A1 (en) | 2015-11-25 | 2018-10-03 | Genentech, Inc. | Substituted benzamides useful as sodium channel blockers |
US10766858B2 (en) | 2016-03-30 | 2020-09-08 | Genentech, Inc. | Substituted benzamides and methods of use thereof |
JP2019519582A (en) | 2016-06-29 | 2019-07-11 | オリオン コーポレーション | Benzodioxane derivative and its pharmaceutical use |
PE20190980A1 (en) | 2016-10-17 | 2019-07-09 | Genentech Inc | THERAPEUTIC COMPOUNDS AND METHODS TO USE THEM |
US10793550B2 (en) | 2017-03-24 | 2020-10-06 | Genentech, Inc. | 4-piperidin-n-(pyrimidin-4-yl)chroman-7-sulfonamide derivatives as sodium channel inhibitors |
CN111918652A (en) | 2017-11-06 | 2020-11-10 | 拉普特医疗公司 | Chemokine receptor modulators for the treatment of epstein-barr virus positive cancers |
EP3759098A1 (en) | 2018-02-26 | 2021-01-06 | Genentech, Inc. | Pyridine-sulfonamide compounds and their use against pain and related conditions |
EP3774801A1 (en) | 2018-03-30 | 2021-02-17 | F. Hoffmann-La Roche AG | Fused ring hydro-pyrido compounds as sodium channel inhibitors |
WO2019236631A1 (en) * | 2018-06-05 | 2019-12-12 | Rapt Therapeutics, Inc. | Pyrazolo-pyrimidin-amino-cycloalkyl compounds and their therapeutic uses |
EP3966209A4 (en) | 2019-05-08 | 2023-01-04 | Vimalan Biosciences, Inc. | Jak inhibitors |
US11453671B2 (en) * | 2019-06-18 | 2022-09-27 | Genentech, Inc. | Pyrazolopyrimidine inhibitors of JAK kinases and uses thereof |
CA3150281A1 (en) * | 2019-08-08 | 2021-02-11 | Vimalan Biosciences, Inc. | Jak inhibitors |
EP4090332A4 (en) * | 2020-01-15 | 2024-02-14 | KSQ Therapeutics, Inc. | Compositions of substituted pyrazolopyrimidines and uses thereof |
TW202233621A (en) * | 2020-10-30 | 2022-09-01 | 美商Ksq治療公司 | Solid state forms of substituted pyrazolopyrimidines and uses thereof |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7138401B2 (en) * | 2003-09-18 | 2006-11-21 | Conforma Therapeutics Corporation | 2-aminopurine analogs having HSP90-inhibiting activity |
CN101056639A (en) * | 2004-09-15 | 2007-10-17 | 詹森药业有限公司 | Thiazolopyridine kinase inhibitors |
AU2006205851A1 (en) * | 2005-01-14 | 2006-07-20 | Janssen Pharmaceutica N.V. | 5-membered annelated heterocyclic pyrimidines as kinase inhibitors |
ES2345997T3 (en) * | 2005-01-14 | 2010-10-07 | Janssen Pharmaceutica Nv | PIRAZOLOPIRAMIDINAS AS INHIBITORS OF THE KINASAS OF THE CELL CYCLE. |
WO2006091737A1 (en) * | 2005-02-24 | 2006-08-31 | Kemia, Inc. | Modulators of gsk-3 activity |
JP2010516812A (en) * | 2007-01-30 | 2010-05-20 | バイオジェン・アイデック・エムエイ・インコーポレイテッド | Mitotic kinase modulators |
-
2008
- 2008-01-30 JP JP2009548286A patent/JP2010516812A/en not_active Withdrawn
- 2008-01-30 CA CA002676665A patent/CA2676665A1/en not_active Abandoned
- 2008-01-30 US US12/525,155 patent/US20100190787A1/en not_active Abandoned
- 2008-01-30 CA CA002676658A patent/CA2676658A1/en not_active Abandoned
- 2008-01-30 WO PCT/US2008/001230 patent/WO2008094602A2/en active Application Filing
- 2008-01-30 JP JP2009548293A patent/JP2010532312A/en not_active Withdrawn
- 2008-01-30 EP EP08724974A patent/EP2108020A2/en not_active Withdrawn
- 2008-01-30 EP EP08724941A patent/EP2108019A2/en not_active Withdrawn
- 2008-01-30 AU AU2008211108A patent/AU2008211108A1/en not_active Abandoned
- 2008-01-30 AU AU2008211172A patent/AU2008211172A1/en not_active Abandoned
- 2008-01-30 US US12/525,174 patent/US20110281821A9/en not_active Abandoned
- 2008-01-30 WO PCT/US2008/001195 patent/WO2008094575A2/en active Application Filing
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP2010532312A5 (en) | ||
JP2010516812A5 (en) | ||
JP5733982B2 (en) | COMPOUND SUPPRESSING CYTOKINE PRODUCTION AND METHOD FOR PREPARING THE SAME | |
JP2010532312A (en) | 1-H-pyrazolo (3,4B) pyrimidine derivatives and their use as modulators of mitotic kinases | |
PT2316831E (en) | 2-(morpholin-4-yl)pyrimidines as phosphotidylinositol (pi) 3-kinase inhibitors and their use in the treatment of cancer | |
JP5656874B2 (en) | Aminoheterocyclic compounds used as PDE9 inhibitors | |
RU2004106783A (en) | 4-AMINO-6-Phenylpyrrolo [2, 3] Pyrimidine Derivatives | |
JP2005514398A5 (en) | ||
DE60005850T2 (en) | IMIDAZO [1,2-A] PYRIDINE AND PYRAZOLO [2,3-A] PYRIDINE DERIVATIVES | |
AU2014373773C1 (en) | Compounds and methods of use | |
JP2010512337A5 (en) | ||
AU2018271284A1 (en) | Pyrimidine FGFR4 inhibitors | |
TWI487701B (en) | Compounds and compositions as protein kinase inhibitors | |
JP5602729B2 (en) | Quinazoline compound, pharmaceutical composition containing the same and therapeutic agent containing the same | |
JP2017125037A (en) | Imidazopyrrolidinone compounds | |
US8815918B2 (en) | Imidazo [2, 1-B] [1, 3, 4] thiadiazole derivatives | |
ZA200502873B (en) | Substituted piperazines (1,4) diaszepines, and 2,5-diazabicyclo (2.2.1) heptanes as histamine H1 and/or H3 antagonists or histamine H3 reverse antagonists | |
ES2759277T3 (en) | Chromen and 1,1a, 2,7b-tetrahydrocyclopropa [c] chromen pyridopirationiniones as gamma-secretase modulators | |
RU2011114559A (en) | Triazine, pyrimidine, pyridine analogs and their use as therapeutic agents and diagnostic tests | |
JP2011510995A5 (en) | ||
HRP20230472T1 (en) | New hydroxyacid derivatives, a process for their preparation and pharmaceutical compositions containing them | |
RU2009106722A (en) | 2,4-SUBSTITUTED QUINAZOLES AS LIPID KINASE INHIBITORS | |
RU2008145662A (en) | PHOSPHOINOSITIDE-3-KINASE INHIBITORS AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM | |
HRP20130106T1 (en) | Imidazotriazines and imidazopyrimidines as kinase inhibitors | |
JP2009519979A5 (en) |